Cyclopropanecarbonyl chloride → HCID 71533378, compound

HRID 2274948Notes

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.C([O-])(O)=O.[Na+].[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1>O.C(OCC)(=O)C>[CH:33]1([C:36]([N:11]2[CH2:12][CH2:13][C:14]3[N:6]([CH2:5][C:4]4[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:3]=4[F:2])[N:7]=[C:8]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=4)[C:18]#[N:19])[C:9]=3[CH2:10]2)=[O:37])[CH2:35][CH2:34]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a 0° C. cold mixture of 3-[1-(2,4-Difluoro-benzyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile, hydrochloride salt (7c) (0.050 g, 0.129 mmol), NaHCO3 (44 mg, 0.517 mmol), water (2 ml) and ethyl acetate (2 ml) was added cyclopropanecarbonyl chloride (13.5 mg, 0.129 mmol) and the mixture was stirred at 25° C. for 16 h. Water was added, the solution was extracted 2 times with ethyl acetate, the combined organic layers were washed once with brine, dried over MgSO4, filtrated and purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid) to give 21 mg of 3-[5-Cyclopropanecarbonyl-1-(2,4-difluoro-benzyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (8c).

Workup

extractionthe solution was extracted 2 times with ethyl acetate
washthe combined organic layers were washed once with brine
dry with materialdried over MgSO4
filtrationfiltrated
custompurified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-1d59f119f5244ff0aba109b1bd4a1724
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09127001B2

Reaction notes

Loading…