5-(4-Carboxyphenyl)-2-hydroxypyridine → HCID 86761324, compound

HRID 551284Notes

Reaction equation

HRID 551284 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[O:17]=[C:18]1[NH:23][CH:22]=[C:21]([C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=2)[CH:20]=[CH:19]1>>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11]3[CH2:16][CH2:15][N:14]([C:28]([C:27]4[CH:26]=[CH:25][C:24]([C:21]5[CH:20]=[CH:19][C:18](=[O:17])[NH:23][CH:22]=5)=[CH:32][CH:31]=4)=[O:29])[CH2:13][CH2:12]3)[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 532177425-(4-Carboxyphenyl)-2-hydroxypyridineHCID 867613214-Chloro-2-piperidin-4-yl-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 86761324HCID 86761324, compound

Procedure

The title compound is prepared as described in EXAMPLE 31, Part K, but with 4-chloro-2-piperidin-4-yl-1H-pyrrolo[3,2-c]pyridine and 4-(6-oxo-1,6-dihydropyridin-3-yl)benzoic acid as starting materials. Purification was by flash column chromatography on silica gel. 1H NMR (d4-MeOH) δ 7.99 (dd, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.66-7.63 (m, 2H), 7.54-7.50 (m, 2H), 7.30 (dd, 1H), 6.65 (d, 1H), 6.41 (s, 1H), 3.96-3.84 (m, 1H), 3.45-3.05 (m, 4H), 2.22-2.01 (m, 2H), 1.92-1.71 (m, 2H). ESI MS (M+1)+: 433, 435 (Cl).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-94d80d7981564f1fac93ee98d586d642
Source dataset
uspto-grants-2011_05
Patent number
US07947684B2

Reaction notes

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