Potassium Carbonate → N-(4-(2-ethyl-5-(5-methyl-1H-pyrazol-3-ylamino)imidazo[1,2-c]pyrimidin-7-ylthio)phenyl)cyclopropanecarboxamide

HRID 2234846Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)[N:5]2[CH:15]=[C:16]([CH2:18][CH3:19])[N:17]=[C:4]2[CH:3]=1.[SH:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([CH:30]2[CH2:32][CH2:31]2)=[O:29])=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:18]([C:16]1[N:17]=[C:4]2[CH:3]=[C:2]([S:20][C:21]3[CH:22]=[CH:23][C:24]([NH:27][C:28]([CH:30]4[CH2:31][CH2:32]4)=[O:29])=[CH:25][CH:26]=3)[N:7]=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=3)[N:5]2[CH:15]=1)[CH3:19]

Participants

Conditions

Temperature: 160 °C

Procedure

7-chloro-2-ethyl-N-(5-methyl-1H-pyrazol-3-yl)imidazo[1,2-c]pyrimidin-5-amine 0.22 mmol, 0.06 g) was dissolved in DMF (1 mL). N-(4-mercaptophenyl)cyclopropanecarboxamide (0.24 mmol, 0.046 g) and K2CO3 (0.24 mmol, 0.033 g) was added. The reaction mixture was heated to 160° C. using a microwave reactor for 20 minutes. The mixture was then concentrated and purified by LC-MS to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.83-0.84 (m, 4H) 1.25 (t, J=7.45 Hz, 3H) 1.79-1.86 (m, 1H) 2.12 (s, 3H) 2.73 (q, J=7.24 Hz, 2H) 5.80 (s, 1H) 6.65 (s, 1H) 7.58 (d, J=8.59 Hz, 2H) 7.81 (d, J=8.59 Hz, 2H) 8.31 (s, 1H) 10.55 (s, 1H) 10.97 (s, 1H) 12.30 (s, 1H); ESI-MS: m/z calc'd for C22H23N7OS 433.53; found 434.4 (M+H)+.

Workup

customfor 20 minutes
concentrationThe mixture was then concentrated
custompurified by LC-MS

Sources & evidence

ORD record: ord-054631939b984b10a81946276a8f313c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713973B2

Reaction notes

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