Chlorosuccinimide → HCID 86689475, compound

HRID 1853725Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]([N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:24][CH3:25])=[CH:19][CH:18]=1.C1C(=O)N([Cl:42])C(=O)C1>>[Cl:42][C:11]1[C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]([C:17]2[CH:22]=[CH:21][C:20]([C@@H:23]([N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])[CH2:24][CH3:25])=[CH:19][CH:18]=2)=[C:3]([O:2][CH3:1])[CH:12]=1

Participants

Reactant 2

HCID 31398Chlorosuccinimide

HCID 86689476HCID 86689476, compound

Product 1

HCID 86689475HCID 86689475, compoundYield 61%

Procedure

Following General Procedure H, ((S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate) (200 mg, 0.41 mmol) was reacted with NCS (68 mg, 0.50 mmol) to afford the desired product (130 mg, 61%) as a yellow solid: ESI MS m/z 513 [C27H29ClN2O4S+H]+.

Sources & evidence

ORD record: ord-aacdfbf5c34a4cb58fcd92355c51fc5f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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