Methanesulfonic Acid → Cyclohexanecarboxylic acid [2-(4-cyclohexanecarbonyl-phenyl)-3h-imidazo[4,5-c]pyridine-6-yl]-amide dimethane sulfonamide salt

HRID 854084Notes

Reaction equation

HRID 854084 reaction equation
[CH:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[NH:32][C:18]4[CH:19]=[N:20][C:21]([NH:23][C:24]([CH:26]5[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]5)=[O:25])=[CH:22][C:17]=4[N:16]=3)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:33][S:34]([OH:37])(=O)=[O:35]>CO>[CH3:33][S:34]([NH2:16])(=[O:37])=[O:35].[CH3:33][S:34]([NH2:16])(=[O:37])=[O:35].[CH:1]1([C:7]([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[NH:32][C:18]4[CH:19]=[N:20][C:21]([NH:23][C:24]([CH:26]5[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]5)=[O:25])=[CH:22][C:17]=4[N:16]=3)=[CH:13][CH:14]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 86592841Cyclohexanecarboxylic acid [2-(4-cyclohexanecarbonyl-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

Product 1

HCID 86592842Cyclohexanecarboxylic acid [2-(4-cyclohexanecarbonyl-phenyl)-3h-imidazo[4,5-c]pyridine-6-yl]-amide dimethane sulfonamide saltYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 11 (0.100 g, 0.225 mmol) in MeOH (5 ml), methanesulfonic acid (0.050 ml) was added and stirred at room temperature for 2 h. The solvents were removed under reduced pressure and acetone and ether were added. The solid was collected by filtration to give the product 12 (0.075 g, 52%). M.p. 258-268° C., 1H NMR (DMSO-d6, 500 MHz): δ 11.49 (1H, brs, NH), 10.25 (1H, brs, NH), 8.79 (1H, s), 8.165 (2H, d, J=9.0 Hz), 7.87 (2H, d, J=9.0 Hz), 8.78 (1H, s), 2.40 (6H, s), 2.37 (2H, m), 1.91-1.20 (20H, m); EIMS m/z: 541.1 (M+CH3SO3H), 446.5 (M+1); Anal. (C28H39N5O8S2×2.20H2O) C, H, N, S

Workup

  1. customThe solvents were removed under reduced pressure and acetone and ether
  2. additionwere added
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-31789938982c4cb99d442f5d828d965f
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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