4-Toluenesulfonyl chloride → HCID 67012524, compound

HRID 2111812Notes

Reaction equation

HRID 2111812 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([N:10]2[C:14]3[CH:15]=[CH:16][C:17]([C:19]([NH:21][CH2:22][C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)=[O:20])=[CH:18][C:13]=3[N:12]=[CH:11]2)[CH:7]=[CH:8][CH:9]=1.[S:29](Cl)([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30].CCN(CC)CC>C1COCC1>[CH3:36][C:35]1[CH:37]=[CH:38][C:32]([S:29]([NH:3][C:4]2[CH:5]=[C:6]([N:10]3[C:14]4[CH:15]=[CH:16][C:17]([C:19]([NH:21][CH2:22][C:23]5[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=5)=[O:20])=[CH:18][C:13]=4[N:12]=[CH:11]3)[CH:7]=[CH:8][CH:9]=2)(=[O:31])=[O:30])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 69067476HCID 69067476, compound

Product 1

HCID 67012524HCID 67012524, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(3-aminophenyl)-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide dihydrochloride (47 mg, 0.14 mmol) and TsCl (27 mg, 0.14 mmol) was dissolved in anhydrous THF (3 mL) at 0° C. and treated with Et3N (95 μL, 0.68 mmol). The reaction mixture was stirred for 72 h and then filtered. The solid residue was washed with THF and the combined washings and filtrate were concentrated in vacuo. The resultant residue was purified by silica gel chromatography (0-7% MeOH in CH2Cl2). Further purification was achieved by trituration with MeOH to afford 1-(3-{[(4-methylphenyl)sulfonyl]amino}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide as a white solid. 1H-NMR (DMSO-d6, 400 MHz): δ 2.35 (s, 3H), 4.54 (d, J=5.6 Hz, 2H), 7.20 (d, J=8.0 Hz, 1H), 7.32-7.44 (m, 4H), 7.50 (t, J=7.6 Hz, 1H), 7.68-7.81 (m, 3H), 7.89 (d, J=8.8 Hz, 1H), 8.36 (s, 1H), 8.47 (brs, 1H), 8.61 (s, 1H), 9.19 (brs, 1H). MS (ES+): m/z 498 [MH+].

Workup

  1. filtrationfiltered
  2. washThe solid residue was washed with THF
  3. concentrationthe combined washings and filtrate were concentrated in vacuo
  4. customThe resultant residue was purified by silica gel chromatography (0-7% MeOH in CH2Cl2)
  5. customFurther purification

Sources & evidence

ORD record
ord-22b30c43978c4fb58b872b4959a36c81
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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