Potassium Carbonate → HCID 59299030, compound

HRID 2234836Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)[N:5]2[CH:15]=[CH:16][N:17]=[C:4]2[N:3]=1.[SH:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([CH:28]2[CH2:30][CH2:29]2)=[O:27])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:14][C:12]1[NH:11][N:10]=[C:9]([NH:8][C:6]2[N:5]3[CH:15]=[CH:16][N:17]=[C:4]3[N:3]=[C:2]([S:18][C:19]3[CH:20]=[CH:21][C:22]([NH:25][C:26]([CH:28]4[CH2:29][CH2:30]4)=[O:27])=[CH:23][CH:24]=3)[CH:7]=2)[CH:13]=1

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of (7-Chloro-imidazo[1,2-a]pyrimidin-5-yl)-(5-methyl-1H-pyrazol-3-yl)-amine (73 mg, 0.29 mmol), N-(4-mercaptophenyl)cyclopropanecarboxamide (170 mg, 0.88 mmol), potassium carbonate (81 mg, 0.58 mmol) in DMF (1 ml) was heated with microwave at 190° C. for 30 minutes. The reaction mixture was then purified by HPLC to give the title compound Example 10 as an off-white solid (110 mg). 1H NMR (400 MHz, DMSO) δ 10.54 (s, 1H) 8.26 (d, J=2.8 Hz, 1H) 7.97 (d, J=2.4 Hz, 1H) 7.79 (d, J=8.8 Hz, 2H) 7.57 (d, J=8.8 Hz, 2H) 6.89 (s, 1H) 5.82 (s, 1H) 2.20 (s, 3H) 1.81-1.85 (m, 1H) 0.84-0.86 (m, 4H). [M+H] calc'd for C20H19N7OS, 406; found, 406.

Workup

customThe reaction mixture was then purified by HPLC

Sources & evidence

ORD record: ord-46d65acd0b774f7cb65de6f43c86ccde
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713973B2

Reaction notes

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