4-(Pyridin-2-yl)-1,3-thiazol-2-amine → HCID 86662348, compound

HRID 1482819Notes

Reaction equation

HRID 1482819 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[N:28]=[C:29]([NH2:32])[S:30][CH:31]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([NH:32][C:29]3[S:30][CH:31]=[C:27]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=4)[N:28]=3)=[O:18])=[CH:19][CH:20]=2)(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10924594-(Pyridin-2-yl)-1,3-thiazol-2-amineHCID 8497540HCID 8497540, compound

Product 1

HCID 86662348HCID 86662348, compound

Procedure

4-(N-(3-chlorophenyl)sulfamoyl)benzoic acid (11) (106 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-(N-(3-chlorophenyl)sulfamoyl)-N-(4-(pyridin-2-yl)thiazol-2-yl)benzamide as a yellow solid. Yield: 49 mg (37%). 1H-NMR: 10.77 (s, 1H), 8.63-8.61 (m, 1H), 8.25 (d, J=8.5 Hz, 2H), 8.00 (d, J=8.0 Hz, 1H), 7.95-7.88 (m, 4H), 7.35 (ddd, J=7.5, 5.0, 1.0 Hz, 1H), 7.30 (t, J=8.0 Hz, 1H), 7.15 (t, J=2 Hz, 1H), 7.13-7.08 (m, 2H), 3.32 (s, 3H).

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-18ca8b6964d74a1ab284cb57005c0e80
Source dataset
uspto-grants-2016_08
Patent number
US09416101B2

Reaction notes

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