Pyrazolo[1,5-a]pyrimidine-3-carbonyl chloride → HCID 49836036, compound

HRID 1466685Notes

Reaction equation

HRID 1466685 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([C:8]2[N:9]=[C:10]([CH3:14])[S:11][C:12]=2[NH2:13])[CH:7]=1.[N:17]1[N:21]2[CH:22]=[CH:23][CH:24]=[N:25][C:20]2=[C:19]([C:26](Cl)=[O:27])[CH:18]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([C:8]2[N:9]=[C:10]([CH3:14])[S:11][C:12]=2[NH:13][C:26]([C:19]2[CH:18]=[N:17][N:21]3[CH:22]=[CH:23][CH:24]=[N:25][C:20]=23)=[O:27])[CH:7]=1

Participants

3

Reactant 2

HCID 19623233Pyrazolo[1,5-a]pyrimidine-3-carbonyl chlorideHCID 66847431HCID 66847431, compound

Product 1

HCID 49836036HCID 49836036, compound

Procedure

Using 4-(5-chloro-2-methoxyphenyl)-2-methylthiazol-5-amine and pyrazolo[1,5-a]pyrimidine-3-carbonyl chloride the title compound was synthesized following the synthetic procedures described for N-(2-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-4-(5-chloro-2-methoxyphenyl)thiazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide with further purification by flash chromatography on silica gel (0 to 100% ethyl aceate in DCM) to give N-(4-(5-chloro-2-methoxyphenyl)-2-methylthiazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide as an orange solid. LCMS (ESI) m+H=400.0; 1H NMR (400 MHz, DMSO-d6): δ 10.43 (s, br, 1H); 9.38 (dd, 1H); 8.75-8.73 (m, 1H); 8.72 (s, 1H); 7.52 (dd, 1H); 7.47 (d, 1H); 7.34-7.32 (m, 2H); 3.79 (s, 3H); 2.62 (s, 3H).

Sources & evidence

ORD record
ord-6caa862542694230a75b21323ee6bd98
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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