2-Thiophenesulfonyl chloride → HCID 67011900, compound

HRID 2111813Notes

Reaction equation

HRID 2111813 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]1[CH:33]=[CH:32][CH:31]=[C:30]1[S:34](Cl)(=[O:36])=[O:35]>N1C=CC=CC=1>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([CH2:22][NH:21][C:19]([C:17]2[CH:16]=[CH:15][C:14]3[N:10]([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([NH:3][S:34]([C:30]5[S:29][CH:33]=[CH:32][CH:31]=5)(=[O:36])=[O:35])[CH:5]=4)[CH:11]=[N:12][C:13]=3[CH:18]=2)=[O:20])[CH:24]=1

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 69067476HCID 69067476, compound

Product 1

HCID 67011900HCID 67011900, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(3-Aminophenyl)-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide dihydrochloride (60 mg, 0.17 mmol) was dissolved in 2 mL pyridine at 0° C. and 2-thiophenesulphonyl chloride (31 mg, 0.17 mmol) was added in one portion to the mixture, and the reaction was stirred room temperature. After 16 h, the reaction mixture was concentrated in vacuo. The residue was purified using the Waters mass-directed HPLC purification system to yield N-pyridin-3-ylmethyl-1-{3-[(thien-2-ylsulfonyl)amino]phenyl}-1H-benzimidazole-5-carboxamide as a white solid. 1H NMR (400 MHz, CD3OD): δ 8.60 (s, 1H), 8.48 (d, J=12.0 Hz, 2H), 8.30 (s, 1H), 7.90 (t, J=8.0 Hz, 2H), 7.69 (d, J=4.0 Hz, 1H), 7.55 (dd, J=1.2 Hz, 4.0 Hz, 1H), 7.48-7.43 (m, 3H), 7.37 (t, J=2.0 Hz, 1H), 7.21 (t, J=8.0 Hz, 1H), 7.09 (t, J=8.0 Hz, 1H), 4.67 (d, J=5.4 Hz, 2H). MS (ES+): m/z 490 [MH+].

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was purified
  3. customthe Waters mass-directed HPLC purification system

Sources & evidence

ORD record
ord-6bc2d764edbb464fa41f797b339baf8a
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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