Cyclohexanecarbonyl chloride → HCID 86592845, compound

HRID 854092Notes

Reaction equation

HRID 854092 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:25][C:11]3[CH:12]=[N:13][C:14]([NH:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[O:18])=[CH:15][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[CH:26]1([C:32](Cl)=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C1COCC1.N1C=CC=CC=1>[CH:26]1([C:32]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[NH:25][C:11]4[CH:12]=[N:13][C:14]([NH:16][C:17]([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=5)=[O:18])=[CH:15][C:10]=4[N:9]=3)=[CH:4][CH:3]=2)=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 58932927Pyridine-2-carboxylic acid [2-(4-amino-phenyl)-3H-imidazo[4,5-c]pyridin-6-yl]-amide

Product 1

HCID 86592845HCID 86592845, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

A solution of amine 22 (0.040 g, 0.12 mmol) and cyclohexane carbonyl chloride (0.100 ml, 0.68 mmol) in dry THF-Pyridine (10 ml/0.300 ml) was stirred at room temperature overnight. A usual work-up as described earlier afforded the diamide 23 (0.025 g, 47%). M.p. 258° C.; 1H NMR (DMSO-d6, 500 MHz): δ 13.5 (1H, brs, NH), 10.60 (1H, brs, NH), 10.13 (1H, brs, NH), 8.78 (1H, d, J=5.0 Hz), 8.74 (1H, brs), 8.46 (1H, brs), 8.24 (1H, d, J=12.5 Hz), 8.115 (2H, d, J=8.0 Hz), 7.81 (2H, d, J=8.0 Hz), 7.74 (1H, dt, J=10.0 and 13.5 Hz), 2.37 (1H, m), 1.84-1.18 (10H, m); EIMS m/z: 441.4 (M+1), 439.6 (M−1); Anal (C25H24N6O2×1.10 H2O) C, H, N.

Sources & evidence

ORD record
ord-dbd946dc67964d3dba20b61e468996db
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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