Methylamine → HCID 71532759, compound

HRID 2274954Notes

Reaction equation

HRID 2274954 reaction equation
Cl.[F:2][C:3]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:4]=1[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][NH:11][CH2:10][C:9]=2[C:8]([C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])=[N:7]1.[CH2:28]([N:30]([CH2:33]C)CC)C.CN.[O:37]1CCCC1>>[CH3:28][NH:30][C:33]([N:11]1[CH2:12][CH2:13][C:14]2[N:6]([CH2:5][C:4]3[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:3]=3[F:2])[N:7]=[C:8]([C:15]3[CH:22]=[CH:21][CH:20]=[C:17]([C:18]#[N:19])[CH:16]=3)[C:9]=2[CH2:10]1)=[O:37]

Participants

5

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 131733416HCID 131733416, compound

Product 1

HCID 71532759HCID 71532759, compoundYield 4.9%

Conditions

Temperature
0 °C

Procedure

To a mixture of 3-[1-(2,4-Difluoro-benzyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (7c) (0.060 g, 0.171 mmol) and triethylamine (60 mg, 0.60 mmol) in CH2C2 at 0° C. was added para-nitrophenylchloroformate (38 mg, 0.188 mmol) and the mixture was stirred at 0° C. for 45 min. 2 M methylamine in tetrahydrofuran (2 ml, 4 mmol) was added and the mixture was stirred for 3 days at room temperature. The crude product was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic) to give 3.4 mg of 3-(3-Cyano-phenyl)-1-(2,4-difluoro-benzyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid methylamide (12a).

Workup

  1. stirringthe mixture was stirred for 3 days at room temperature
  2. customThe crude product was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic)

Sources & evidence

ORD record
ord-795706ec78df48d6aa55067d97ca62b8
Source dataset
uspto-grants-2015_09
Patent number
US09127001B2

Reaction notes

Loading…