Trifluoroacetic acid → HCID 11397081, compound

HRID 916184Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH:6]=1)=[O:4].[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25].C(O)(C(F)(F)F)=O>>[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([CH2:14][N:7]3[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5]([C:3]([OH:2])=[O:4])=[CH:6]3)=[CH:16][CH:17]=2)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 1398824-t-Butylbenzenesulfonyl chloride

HCID 69438464HCID 69438464, compound

Product 1

HCID 11397081HCID 11397081, compound

Procedure

The title compound was prepared from 1-(4-nitro-benzyl)-1H-indole-3-carboxylic acid methyl ester and 4-tert-butylbenzenesulfonyl chloride followed the procedure of Example 3 Step 2 as a light brown solid: 1H NMR (DMSO-d6) δ 1.24 (s, 9H), 5.36 (s, 2H), 7.04 (d, J=8.5 Hz, 2H), 7.13-7.18 (m, 4H), 7.45 (dd, J=6.1, 2.6 Hz, 1H), 7.52 (d, J=8.8 Hz, 2H), 7.66 (d, J=8.8 Hz, 2H), 8.00 (dd, J=6.1, 2.6 Hz, 1H), 8.13 (s, 1H), 10.23 (br s, 1H), 11.98 (br s, 1H); MS (ESI) m/z 463 (MH+), 461 ([M−H]−); HRMS calcd for C26H27N2O4S: 463.1690; found (ESI+): 463.1681; Anal. calcd for C26H26N2O4S.0.06 TFA: C, 67.51; H, 5.67; N, 6.06. Found: C, 67.40; H, 5.65; N, 6.04.

Sources & evidence

ORD record: ord-10e1be99c4f043a683489b9297bb1e2d
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268159B2

Reaction notes

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