4-(Pyridin-2-yl)-1,3-thiazol-2-amine → HCID 86662347, compound

HRID 1482814Notes

Reaction equation

HRID 1482814 reaction equation
[N:1]1([S:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[C:16]([F:23])[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.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[N:31]=[C:32]([NH2:35])[S:33][CH:34]=1>>[N:1]1([S:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([NH:35][C:32]3[S:33][CH:34]=[C:30]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=4)[N:31]=3)=[O:19])=[C:16]([F:23])[CH:15]=2)(=[O:12])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 10924594-(Pyridin-2-yl)-1,3-thiazol-2-amineHCID 66762941HCID 66762941, compound

Product 1

HCID 86662347HCID 86662347, compound

Procedure

4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)-2-fluorobenzoic acid (9) (160 mg, 0.48 mmol) was treated with 4-(pyridin-2-yl)thiazol-2-amine (70 mg, 0.40 mmol) using method C. The residue was purified using flash chromatography eluting with EtOAc. The resulting solid was triturated with diethyl ether to give 4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)-2-fluoro-N-(4-(pyridin-2-yl)thiazol-2-yl)benzamide as an off white solid. Yield: 38 mg (19%). 1H-NMR: 8.63-8.60 (m, 1H), 7.98-7.85 (m, 4H), 7.61 (d, J=8.5 Hz, 2H), 7.52 (dd, J=8.5, 2.0 Hz, 1H), 7.35 (ddd, J=7.5, 5.0, 1.0 Hz, 1H), 7.26-7.20 (m, 1H), 7.15-7.12 (m, 2H), 3.87-3.82 (m, 2H), 2.51-2.47 (m, 2H), 1.71-1.63 (m, 2H).

Workup

  1. customThe residue was purified
  2. washeluting with EtOAc
  3. customThe resulting solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-1b0a5ba83410441da8541af1fb61d8f9
Source dataset
uspto-grants-2016_08
Patent number
US09416101B2

Reaction notes

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