Benzenesulfonyl chloride → HCID 11432932, compound

HRID 2118132Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([C:24]([O:26]CC)=[O:25])=[C:5]2[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:35]1([S:41](Cl)(=[O:43])=[O:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[CH:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][S:41]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)(=[O:43])=[O:42])=[CH:10][CH:9]=2)[C:5]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:6]1[C:24]([OH:26])=[O:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Reactant 2

HCID 7369Benzenesulfonyl chloride

HCID 69227813HCID 69227813, compound

Product 1

HCID 11432932HCID 11432932, compound

Procedure

The title compound was prepared from ethyl 5-amino-1-benzhydryl-3-phenyl-1H-indole-2-carboxylate and phenylsulfonyl chloride followed the procedure of Example 1 Step 3 as a pale yellow solid: 1H NMR (DMSO-d6) δ 6.68 (d, J=9.0 Hz, 1H, 6.78 (dd, J=9.2, 2.2 Hz, 1H), 7.04 (d, J=2.2 Hz, 1H, 7.13 (d, J=7.1 Hz, 4H, 7.25-7.30 (m, 2H, 7.30-7.40 (m, 7H, 7.40-7.55 (m, 4H, 7.58-7.68 (m, 3H, 7.84 (s, 1H, 9.93 (s, 1H, 13.19 (br s, 1H; MS (ESI) m/z 557 [M-H]−; HRMS calcd for C34H27N2O4S: 559.1689; found (ESI+): 559.1686; Anal. calcd for C34H26N2O4S.0.6H2O: C, 71.71; H, 4.81; N, 4.92. Found: C, 71.51; H, 4.77; N, 5.11.

Sources & evidence

ORD record: ord-51ea55545b5a4ddd98ecf53ab2b432f5
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442805B2

Reaction notes

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