2-Pyridinecarboxaldehyde → HCID 178423678, compound

HRID 1991957Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[CH:20]=[C:19]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH:18]=[CH:17][C:16]=2[NH:27][C:28]([C:30]2[NH:31][CH:32]=[C:33]([C:35]#[N:36])[N:34]=2)=[O:29])=[CH:11][CH2:10]1.[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH:43]=O>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[CH:20]=[C:19]([CH:21]3[CH2:22][CH2:23][N:24]([CH2:43][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][N:37]=4)[CH2:25][CH2:26]3)[CH:18]=[CH:17][C:16]=2[NH:27][C:28]([C:30]2[NH:31][CH:32]=[C:33]([C:35]#[N:36])[N:34]=2)=[O:29])=[CH:11][CH2:10]1

Participants

Reactant 2

HCID 142732-Pyridinecarboxaldehyde

HCID 178423676HCID 178423676, compound

Product 1

HCID 178423678HCID 178423678, compound

Procedure

This compound was prepared according to the procedure in Example 21 from 4-cyano-1H-imidazole-2-carboxylic acid [2-(4-methyl-cyclohex-1-enyl)-4-piperidin-4-yl-phenyl]-amide (as prepared in Example 17) and pyridine-2-carbaldehyde. 1H-NMR (400 MHz, DMSO-d6): δ 14.25 (br s, 1H), 9.90 (br s, 1H), 9.79 (s, 1H), 8.72 (s, 1H), 8.36 (s, 1H), 7.98 (m, 1H), 7.86 (dd, 1H), 7.54 (d, 1H), 7.52 (m, 1H), 7.20 (m, 1H), 7.12 (d, 1H), 5.74 (m, 1H), 4.56 (s, 2H), 3.40 (m, 2H), 3.18 (m, 2H), 2.88 (m, 1H), 2.48-2.22 (m, 3H), 2.18-2.06 (m, 4H), 1.98-1.82 (m, 3H), 1.52 (m, 1H), 1.02 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C28H32N6O, 481.2 (M+H), found 481.2.

Workup

customThis compound was prepared

Sources & evidence

ORD record: ord-04637628e87c4516bd3c38295b9261cc
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645755B2

Reaction notes

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