2-Aminothiazole → HCID 59252784, compound

HRID 563448Notes

Reaction equation

[CH3:1][C:2]([CH3:28])([CH:6]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:7]1[CH:8]=[C:9]2[CH:15]=[N:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]2=[N:11][CH:12]=1)[C:3](O)=[O:4].[NH2:29][C:30]1[S:31][CH:32]=[CH:33][N:34]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.FC(F)(F)C(O)=O>CN(C=O)C>[CH3:28][C:2]([CH3:1])([CH:6]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:7]1[CH:8]=[C:9]2[CH:15]=[N:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]2=[N:11][CH:12]=1)[C:3]([NH:29][C:30]1[S:31][CH:32]=[CH:33][N:34]=1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 2,2-dimethyl-3-phenyl-3-(1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)propanoic acid (8 mg, 0.022 mmol), 2-aminothiazole (9 mg, 0.09 mmol), and diisopropylethylamine (0.015 mL, 0.09 mmol) in anhydrous DMF (0.3 mL) was added HATU (33 mg, 0.09 mmol) under argon. After stirred at rt overnight and 80° C. for 30 min, the mixture was concentrated. HPLC purification gave 2,2-dimethyl-3-phenyl-3-(1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-N-(thiazol-2-yl)propanamide (Example 162, 5 mg, 0.009 mmol, 41% yield) as a trifluoroacetic acid salt. MS found: (M−H)−=452.11. 1H-NMR (400 MHz, Acetone) δ ppm 8.56 (1 H, d, J=2.54 Hz) 8.39 (1H, d, J=2.03 Hz) 8.24 (2H, d, J=7.63 Hz) 8.18 (1H, s), 7.37-7.47 (4H, m) 7.27 (1H, d, J=3.56 Hz) 7.16-7.23 (3H, m) 7.11 (1H, t, J=7.38 Hz) 6.95 (1H, d, J=3.56 Hz) 4.98 (1H, s) 1.42 (6H, d, J=7.63 Hz).

Workup

concentrationthe mixture was concentrated
customHPLC purification

Sources & evidence

ORD record: ord-82ae84d781e741cdacb831fa17a3c2ac
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067447B2

Reaction notes

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