Hydrochloric Acid → HCID 22617857, compound

HRID 842025Notes

Reaction equation

HRID 842025 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[C:11]1[C:12]([CH3:25])=[N:13][N:14]2[C:19](NCCN)=[CH:18][C:17]([CH3:24])=[N:16][C:15]=12.O1CCC(=O)CC1.C([BH3-])#N.[Na+].[ClH:37]>CO.CCOCC.C(O)(=O)C>[Cl:37][C:19]1[N:14]2[N:13]=[C:12]([CH3:25])[C:11]([C:3]3[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH3:9])=[CH:5][C:4]=3[Cl:10])=[C:15]2[N:16]=[C:17]([CH3:24])[CH:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5003444Sodium cyanoborohydrideHCID 22617879HCID 22617879, compound

Product 1

HCID 22617857HCID 22617857, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of N-[3-(2,6-dichloro-4-methoxy-phenyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-ethane-1,2-diamine (3.32 g, 8.7 mmol) and tetrahydro-4H-pyran-4-one (1.8 g, 18 mmol) in methanol (60 mL)/acetic acid (1.6 g) was added sodium cyanoborohydride (1.1 g, 17 mmol), portionwise. After stirring 1 hour the reaction was concentrated under reduced pressure and then extracted from saturated aqueous sodium bicarbonate with ethyl acetate. The combined extracts were dried (Na2SO4), concentrated under reduced pressure to give the crude product as a colorless foam (4.1 g, quant). A solution of the product in ether (150 mL) was treated with 1 M ethereal HCl which generated a precipitate that was collected by vacuum filtration to give the title compound (4.1 g, 94%) as a pink solid: +APcI MS (M+1)+464; 1H NMR (methanol-d4) δ: 7.14 (s, 2H), 6.38 (s, 1H), 4.03 (dd, 2H), 3.94 (br t, 2H), 3.86 (s, 3H), 3.50-3.38 (m, 5H), 2.51 (s, 3H), 2.26 (s, 3H), 2.05 (m, 2H), 1.68 (qd, 2H).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. extractionextracted from saturated aqueous sodium bicarbonate with ethyl acetate
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product as a colorless foam (4.1 g, quant)
  6. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-e7332dcca079459baa7410deb26c850a
Source dataset
uspto-grants-2002_04
Patent number
US06372743B1

Reaction notes

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