34576-94-8 → HCID 70598680, compound

HRID 1479903Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[CH:24]=[CH:23][C:22](C)=[CH:21][C:4]=2[S:5][C:6]=1[C:7]([NH:9][C@H:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12])=[O:8].[Cl:26]C1C2C=CC(Cl)=CC=2SC=1C(O)=O>>[Cl:1][C:2]1[C:3]2[CH:24]=[CH:23][C:22]([Cl:26])=[CH:21][C:4]=2[S:5][C:6]=1[C:7]([NH:9][C@H:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12])=[O:8]

Participants

Reactant 2

HCID 73988434576-94-8

HCID 70598307HCID 70598307, compound

Product 1

HCID 70598680HCID 70598680, compound

Procedure

Following the 2a synthetic method, using 3,6-dichlorobenzo[b]thiophene-2-carboxylic acid (123.55 mg, 0.5 mmol) instead of 3-chloro-6-methylbenzo[b]thiophene-2-carboxylic acid gave 3a as a white powder; (182.94 mg, 92.8%). [α]D25: −23.2 (c=0.24, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 8.79 (s, 1H), 7.78 (d, J=1.5 Hz, 1H), 7.71 (d, J=8.7 Hz, 1H), 7.59 (d, J=6.9 Hz, 1H), 7.42 (dd, J=1.8, 8.7 Hz, 1H), 7.37-7.25 (m, 5H), 5.16-5.14 (m, 1H), 3.41-3.28 (m, 2H); 13C NMR (300 MHz, CDCl3): δ 175.51, 160.41, 138.97, 135.33, 135.18, 134.21, 132.38, 129.47, 128.82, 127.52, 126.51, 124.16, 122.38, 119.64, 54.12, 37.28; HRMS (ESI): calcd for: C18H13Cl2NO3S [M−H]−=391.9920, obsd [M−H]−=391.9921.

Sources & evidence

ORD record: ord-7b736f5dc510418592ee66272af98554
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409880B2

Reaction notes

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