4-(Pyridin-2-yl)-1,3-thiazol-2-amine → HCID 86662353, compound

HRID 1482836Notes

Reaction equation

HRID 1482836 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([S:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:8][CH2:7][CH2:6]2.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[N:32]=[C:33]([NH2:36])[S:34][CH:35]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([S:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:36][C:33]3[S:34][CH:35]=[C:31]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=4)[N:32]=3)=[O:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:8][CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 10924594-(Pyridin-2-yl)-1,3-thiazol-2-amineHCID 45321020HCID 45321020, compound

Product 1

HCID 86662353HCID 86662353, compound

Procedure

4-(6-methoxy-3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzoic acid (17) (118 mg, 0.34 mmol) was treated with 4-(pyridin-2-yl)thiazol-2-amine (50 mg, 0.28 mmol) using method C. The residue was purified using flash chromatography eluting with 50-100% EtOAc in hexanes. The resulting solid was triturated with diethyl ether to give 4-(6-methoxy-3,4-dihydroquinolin-1(2H)-ylsulfonyl)-N-(4-(pyridin-2-yl)thiazol-2-yl)benzamide as an off-white solid. Yield: 56 mg (39%). 1H-NMR: 8.64-8.61 (m, 1H), 8.21 (d, J=8.5 Hz, 2H), 8.01 (d, J=7.5 Hz, 1H), 7.94-7.88 (m, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.58-7.45 (m, 2H), 7.35 (ddd, J=7.5, 5.0, 1.0 Hz, 1H), 6.83 (dd, J=9.0, 3.0 Hz, 1H), 6.67 (d, J=3.0 Hz, 1H), 3.79-3.70 (m, 5H), 2.33 (t, J=7.0, 2H), 1.57-1.48 (m, 2H).

Workup

  1. customThe residue was purified
  2. washeluting with 50-100% EtOAc in hexanes
  3. customThe resulting solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-fa93c4c52bf7417ab8bd7940120dcf65
Source dataset
uspto-grants-2016_08
Patent number
US09416101B2

Reaction notes

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