2-Amino-6-fluorobenzothiazole → HCID 16832297, compound

HRID 1482839Notes

Reaction equation

HRID 1482839 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.[F:23][C:24]1[CH:33]=[CH:32][C:27]2[N:28]=[C:29]([NH2:31])[S:30][C:26]=2[CH:25]=1>>[N:1]1([S:11]([C:14]2[CH:15]=[CH:16][C:17]([C:18]([NH:31][C:29]3[S:30][C:26]4[CH:25]=[C:24]([F:23])[CH:33]=[CH:32][C:27]=4[N:28]=3)=[O:19])=[CH:21][CH:22]=2)(=[O:12])=[O:13])[C:2]2[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:8][CH2:9][CH2:10]1

Participants

3

Reactant 2

HCID 3199542-Amino-6-fluorobenzothiazoleHCID 23189394-(1,2,3,4-Tetrahydroquinoline-1-sulfonyl)benzoic acid

Product 1

HCID 16832297HCID 16832297, compound

Procedure

4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzoic acid (1) (100 mg, 0.32 mmol) was treated with 6-fluorobenzo[d]thiazol-2-amine (41 mg, 0.24 mmol) using method B. The residue was purified using flash chromatography eluting with 0-40% EtOAc in hexanes to give 4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)-N-(6-fluorobenzo[d]thiazol-2-yl)benzamide as an off-white solid. Yield: 22 mg (19%). 1H-NMR: 8.22 (d, J=8.5 Hz, 2H), 7.94 (dd, J=8.5, 2.5 Hz, 1H), 7.84-7.75 (m, 3H), 7.61 (d, J=8.5 Hz, 2H), 7.33 (dt, J=9.0, 3.0 Hz, 1H), 7.24-7.19 (m, 1H), 7.14-7.08 (m, 2H), 3.84-3.80 (m, 2H), 2.45 (t, J=7.0 Hz, 2H), 1.66-1.58 (m, 2H).

Workup

  1. customThe residue was purified
  2. washeluting with 0-40% EtOAc in hexanes

Sources & evidence

ORD record
ord-8df731cfeb03409c9935c18aecbae335
Source dataset
uspto-grants-2016_08
Patent number
US09416101B2

Reaction notes

Loading…