Benzo(d)thiazol-2-amine → HCID 5145037, compound

HRID 1482837Notes

Reaction equation

HRID 1482837 reaction equation
[N:1]1([S:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[S:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[C:24]1[NH2:32]>>[S:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[C:24]1[NH:32][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([S:11]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)(=[O:12])=[O:13])=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 8706Benzo(d)thiazol-2-amineHCID 23189394-(1,2,3,4-Tetrahydroquinoline-1-sulfonyl)benzoic acid

Product 1

HCID 5145037HCID 5145037, compound

Procedure

4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzoic acid (1) (100 mg, 0.32 mmol) was treated with benzo[d]thiazol-2-amine (39 mg, 0.26 mmol) using method B. The residue was purified using flash chromatography eluting with 0-20% EtOAc in hexanes to give N-(benzo[d]thiazol-2-yl)-4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzamide as an off-white solid. Yield: 29 mg (25%). 1H-NMR: 8.22 (d, J=8.5 Hz, 2H), 8.02 (d, J=8.0 Hz, 1H), 7.73 (d, J=8.5 Hz, 2H), 7.62 (d, J=8.0 Hz, 1H), 7.50-7.45 (m, 1H), 7.37-7.32 (m, 1H), 7.24-7.19 (m, 1H), 7.14-7.08 (m, 2H), 3.84-3.80 (m, 2H), 2.44 (t, J=7.0 Hz, 2H), 1.66-1.58 (m, 2H).

Workup

  1. customThe residue was purified
  2. washeluting with 0-20% EtOAc in hexanes

Sources & evidence

ORD record
ord-6406b02da4174bfcac0f0c57f389241e
Source dataset
uspto-grants-2016_08
Patent number
US09416101B2

Reaction notes

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