Cyclopropanecarboxaldehyde → HCID 118483449, compound

HRID 58469Notes

Reaction equation

Cl.[F:2][C:3]1[C:4]([C:26]([F:29])([F:28])[F:27])=[C:5]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[C:25]4[CH2:24][CH2:23][NH:22][CH2:21][C:20]=4[NH:19][N:18]=3)=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[CH:30]1([CH:33]=O)[CH2:32][CH2:31]1.C(N1CCC2C(C(N3CCC(C4C=CC=C(F)C=4C(F)(F)F)CC3)=O)=NNC=2C1)C>>[CH:30]1([CH2:33][N:22]2[CH2:23][CH2:24][C:25]3[C:17]([C:15]([N:12]4[CH2:11][CH2:10][CH:9]([C:5]5[CH:6]=[CH:7][CH:8]=[C:3]([F:2])[C:4]=5[C:26]([F:29])([F:27])[F:28])[CH2:14][CH2:13]4)=[O:16])=[N:18][NH:19][C:20]=3[CH2:21]2)[CH2:32][CH2:31]1

Participants

Reactant 3

HCID 123114Cyclopropanecarboxaldehyde

HCID 118483339(4-(3-Fluoro-2-(trifluoromethyl)phenyl)piperidin-1-yl)(4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3-yl)methanone Hydrochloride

HCID 118483518HCID 118483518, compound

Product 1

HCID 118483449HCID 118483449, compound

Procedure

Following general procedure GP-G1, ((4-(3-fluoro-2-(trifluoro-methyl)phenyl)piperidin-1-yl)(4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3-yl)methanone hydrochloride (30) and cyclopropane carbaldehyde were converted to (6-ethyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3-yl)(4-(3-fluoro-2-(trifluormethyl)phenyl) piperidin-1-yl)methanone as a white solid (23 mg, 34%): 1H NMR (300 MHz, DMSO-d6) δ 12.74 (br s, 1H), 7.72-7.65 (m, 1H), 7.47 (d, J=7.8 Hz, 1H), 7.34-7.27 (m, 1H), 4.92-4.63 (m, 2H), 3.59-3.53 (m, 2H), 3.32-3.09 (m, 2H), 2.90-2.39 (m, 7H), 1.81-1.62 (m, 4H), 0.92-0.85 (m, 1H), 0.52-0.48 (m, 2H), 0.14-0.10 (m, 2H); ESI MS m/z 451 [M+H]+.

Sources & evidence

ORD record: ord-aa2e72c91a544f47ae5e3580a12a78e6
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434727B2

Reaction notes

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