Triethylamine → N-(cyclopropylmethyl)-1-[(6-methoxy-5-methyl-pyrimidin-4-yl)methyl]pyrrolo[3,2-b]pyridine-3-carboxamide

HRID 1753230Notes

Reaction equation

HRID 1753230 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]([OH:21])=O)=[CH:11]2)[C:4]=1[CH3:22].CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.C(N(CC)CC)C.[CH:48]1([CH2:51][NH2:52])[CH2:50][CH2:49]1>C(Cl)Cl.O>[CH:48]1([CH2:51][NH:52][C:19]([C:12]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:18]3[N:10]([CH2:9][C:5]3[C:4]([CH3:22])=[C:3]([O:2][CH3:1])[N:8]=[CH:7][N:6]=3)[CH:11]=2)=[O:21])[CH2:50][CH2:49]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 75646CyclopropanemethanamineHCID 111923Propylphosphonic anhydrideHCID 1178190601-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid

Product 1

HCID 72792632N-(cyclopropylmethyl)-1-[(6-methoxy-5-methyl-pyrimidin-4-yl)methyl]pyrrolo[3,2-b]pyridine-3-carboxamideYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

See FIG. 16(b). 1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (200 mg, 0.67 mmol) was taken in DCM (10 mL). Added 1-Propanephosphonic acid cyclic anhydride (427 mg, 1.34 mmol) followed by the addition of Triethyl amine (339 mg, 3.35 mmol) and cyclopropylmethanamine (95 mg, 1.34 mmol). The reaction mass was stirred at RT for overnight. After the completion of the reaction added water and extracted with DCM. The organic layer was washed with water and brine solution. The organic layer was separated, dried over sodium sulphate. Evaporated the organic layer to get the residue, which was purified by column chromatography to get the pure compound. Yield-74%. ES+MS m/z: 352.38 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.02 (q, J=4.58 Hz, 2 H ) 0.18-0.31 (m, 2 H ) 0.83 (t, J=6.88 Hz, 1 H ) 2.00 (s, 3 H ) 2.98-3.11 (m, 3 H ) 3.69 (s, 3 H ) 5.43 (s, 2 H ) 7.00 (dd, J=8.29, 4.71 Hz, 1 H ) 7.68 (dd, J=8.29, 1.13 Hz, 1 H ) 7.98 (s, 1 H ) 8.17 (s, 1 H) 8.24 (dd, J=4.71, 1.13 Hz, 1 H ) 8.55 (t, J=5.75 Hz, 1 H ).

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with water and brine solution
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. customEvaporated the organic layer
  6. customto get the residue, which
  7. customwas purified by column chromatography
  8. customto get the pure compound

Sources & evidence

ORD record
ord-a6805d14ffba419fbdc088979a71765d
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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