Methanol → HCID 178480098, compound

HRID 1766169Notes

Reaction equation

HRID 1766169 reaction equation
CO.[Na].Cl.[NH2:5][C:6]([NH2:8])=[NH:7].Cl[C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:21]2[C:22]3[CH:29]=[CH:28][N:27]([CH3:30])[C:23]=3[N:24]=[CH:25][N:26]=2)[CH:13]=1)=[O:11]>ClCCl>[CH3:30][N:27]1[C:23]2[N:24]=[CH:25][N:26]=[C:21]([N:14]3[C:15]4=[N:16][CH:17]=[CH:18][CH:19]=[C:20]4[C:12]([C:10]([NH:7][C:6]([NH2:8])=[NH:5])=[O:11])=[CH:13]3)[C:22]=2[CH:29]=[CH:28]1

Participants

6

Reactant 4

HCID 887MethanolHCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 211100673-chlorocarbonyl-1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 178480098HCID 178480098, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To 40 cm3 of methanol at about 20° C. under argon atmosphere, was added portionwise 0.36 g (16 mmol) of sodium. Then, after total consumption of the latter, 1.5 g (16 mmol) of guanidine hydrochloride were added. The reaction mixture was stirred at about 20° C. for 1.5 hours and filtered. The precipitate was washed with 5 cm3 of methanol and the combined filtrates were concentrated to dryness in vacuo (2.7 kPa). The residue was diluted in 30 cm3 of dichloromethane and concentrated to dryness in vacuo (2.7 kPa). The residue was diluted in 70 cm3 of tetrahydrofuran under argon atmosphere at about 20° C. and a suspension of 1.3 g (3.2 mmol) of 3-chlorocarbonyl-1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine in 70 cm3 of dichloromethane was added. The reaction mixture was stirred at about 20° C. for 60 hours and then concentrated to dryness in vacuo (2.7 kPa). The residue was diluted in 100 cm3 of water and the off-white precipitate was filtered and washed twice with 10 cm3 of water. The solid was dried in vacuo at about 50° C. and then recrystallized from 30 cm3 of methanol. The precipitate was washed twice with 5 cm3 of methanol and once with 10 cm3 of diisopropylether respectively, and dried in vacuo at about 50° C. to yield 0.45 g of N-[1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-guanidine as a gray cristalline powder: mp>260° C. IR spectrum (KBr): 3425; 3157; 1590; 1558; 1518; 1449; 1418; 1308; 1216; 1009; 805; 770; 723; 702 and 605 cm−1. Mass spectrum (EI): m/e 334 M+., m/e 276 (M−CH4N3)+. (base peak), m/e 145 (m/e=276−C7H5N3)+, m/e 132 (C7H6N3)+.

Workup

  1. additionwere added
  2. filtrationfiltered
  3. washThe precipitate was washed with 5 cm3 of methanol
  4. concentrationthe combined filtrates were concentrated to dryness in vacuo (2.7 kPa)
  5. additionThe residue was diluted in 30 cm3 of dichloromethane
  6. concentrationconcentrated to dryness in vacuo (2.7 kPa)
  7. additionThe residue was diluted in 70 cm3 of tetrahydrofuran under argon atmosphere at about 20° C.
  8. additionwas added
  9. stirringThe reaction mixture was stirred at about 20° C. for 60 hours
  10. concentrationconcentrated to dryness in vacuo (2.7 kPa)
  11. additionThe residue was diluted in 100 cm3 of water
  12. filtrationthe off-white precipitate was filtered
  13. washwashed twice with 10 cm3 of water
  14. customThe solid was dried in vacuo at about 50° C.
  15. customrecrystallized from 30 cm3 of methanol
  16. washThe precipitate was washed twice with 5 cm3 of methanol and once with 10 cm3 of diisopropylether respectively
  17. customdried in vacuo at about 50° C.

Sources & evidence

ORD record
ord-65c89432578940feb525c809c8269910
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

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