5-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride → Tert-butyl 3-(3-(5-chloro-3-methylbenzo[b]thiophene-2-sulfonamido)phenyl)azetidine-1-carboxylate

HRID 238976Notes

Reaction equation

HRID 238976 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:19][C:20]1[CH:33]=[CH:32][C:23]2[S:24][C:25]([S:28](Cl)(=[O:30])=[O:29])=[C:26]([CH3:27])[C:22]=2[CH:21]=1>>[Cl:19][C:20]1[CH:33]=[CH:32][C:23]2[S:24][C:25]([S:28]([NH:1][C:2]3[CH:3]=[C:4]([CH:8]4[CH2:9][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:11]4)[CH:5]=[CH:6][CH:7]=3)(=[O:29])=[O:30])=[C:26]([CH3:27])[C:22]=2[CH:21]=1

Participants

3

Reactant 2

HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chlorideHCID 46941930TERT-BUTYL 3-(3-AMINOPHENYL)AZETIDINE-1-CARBOXYLATE

Product 1

HCID 68950293Tert-butyl 3-(3-(5-chloro-3-methylbenzo[b]thiophene-2-sulfonamido)phenyl)azetidine-1-carboxylateYield 71%

Procedure

Following the same procedure as described in Example 1.7, tert-butyl 3-(3-aminophenyl)azetidine-1-carboxylate (100 mg, 0.40 mmol) was coupled with 5-chloro-3-methylbenzo[b]thiophene-2-sulfonyl chloride (118 mg, 0.42 mmol) to give tert-butyl 3-(3-(5-chloro-3-methylbenzo[b]thiophene-2-sulfonamido)phenyl)azetidine-1-carboxylate (140 mg, 71%).

Sources & evidence

ORD record
ord-f96f5bc2603e428595b48c08348382b4
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

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