5-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride → HCID 22015377, compound

HRID 8328Notes

Reaction equation

HRID 8328 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][NH:18]3)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.[Cl:23][C:24]1[CH:25]=[CH:26][C:27]2[S:31][C:30]([S:32](Cl)(=[O:34])=[O:33])=[C:29]([CH3:36])[C:28]=2[CH:37]=1>>[ClH:23].[Cl:23][C:24]1[CH:25]=[CH:26][C:27]2[S:31][C:30]([S:32]([N:18]3[C:19]4[C:15](=[C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)[CH:22]=[CH:21][CH:20]=4)[CH:16]=[CH:17]3)(=[O:34])=[O:33])=[C:29]([CH3:36])[C:28]=2[CH:37]=1

Participants

3

Reactant 2

HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chlorideHCID 22015386tert-Butyl 4-(1H-indol-4-yl)piperazine-1-carboxylate

Product 1

HCID 22015377HCID 22015377, compound

Procedure

The title compound was prepared 4-(4-boc-piperazinyl)-indole and 1-[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl chloride according to Method 4 to afford the hydrochloride salt (yield 45%), HPLC purity >95%; 1H NMR (DMSO-d6) δ 2.65 (s, 3H), 3.26 (bs, 8H), 6.82 (app d, 1H), 7.00 (appd, 1H), 7.28 (app t, 1H), 7.60 (app dd, 2H), 7.87 (app d, 1H), 8.08–8.12 (m, 2H); 13C NMR (DMSO-d6) δ 145.05, 139.82, 139.35, 137.46, 135.14, 133.31, 130.96, 128.70 (2C), 125.62, 124.89, 124.12, 123.52, 111.42, 107.91, 107.71, 47.87 (2C), 43.03 (2C), 12.27; MS (posES-FIA) m/z 446 (M+H).

Sources & evidence

ORD record
ord-b9b26d41593d4cbf888182452c0f1ba4
Source dataset
uspto-grants-2006_08
Patent number
US07087750B2

Reaction notes

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