2-Thiophenesulfonyl chloride → HCID 46908829, compound

HRID 1410205Notes

Reaction equation

HRID 1410205 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].[NH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:39])=[C:16]([NH:18][C:19]2[N:23]([CH3:24])[C:22]3[CH:25]=[CH:26][C:27]([C:29]([NH:31][CH2:32][CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[O:30])=[CH:28][C:21]=3[N:20]=2)[CH:17]=1>CC#N.C(Cl)Cl>[Cl:39][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][NH:10][S:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)(=[O:8])=[O:7])=[CH:17][C:16]=1[NH:18][C:19]1[N:23]([CH3:24])[C:22]2[CH:25]=[CH:26][C:27]([C:29]([NH:31][CH2:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[O:30])=[CH:28][C:21]=2[N:20]=1

Participants

5

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 68512212HCID 68512212, compound

Product 1

HCID 46908829HCID 46908829, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Thiophene-2-sulfonyl chloride (64 mg, 0.35 mmol) in MeCN (1 mL) was added to a mixture of 2-(5-aminomethyl-2-chlorophenylamino)-N-cyclohexylmethyl-1-methylbenzimidazole-5-carboxamide (150 mg, 0.35 mmol), TEA (150 L, 1.1 mmol) and MeCN (2 mL). After 12 h at rt the mixture was diluted with DCM and washed with NH3 (aq, sat) and brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography to give the title compound. Yield: 36 mg (18%). 200 MHz 1H-NMR (DMSO-d6, ppm) 8.50-8.36 (2H, m) 8.35-8.22 (1H, m) 7.94-7.82 (3H, m) 7.69-7.57 (2H, m) 7.42 (1H, d, J=8.2 Hz) 7.37 (1H, d, J=8.2 Hz) 7.18-7.11 (1H, m) 7.04-6.95 (1H, m) 4.09-3.96 (2H, m) 3.71 (3H, s) 3.14-3.00 (2H, m) 1.77-1.47 (7H, m) 1.29-1.07 (4H, m). MS m/z: 572 [M+H]+.

Workup

  1. washwashed with NH3 (aq, sat) and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-82f1f9479a8648c2bedf1c9e0e72f4f9
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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