Dichloromethane → N'-acetyl-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carbohydrazide

HRID 1852999Notes

Reaction equation

[CH3:1][Si:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[N:17]3[CH:18]=[CH:19][N:20]=[C:16]3[CH:15]=[C:14]([C:21]([NH:23][NH2:24])=[O:22])[N:13]=2)[CH:9]=[N:8]1.C(Cl)Cl.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38]>CCOC(C)=O>[C:37]([NH:24][NH:23][C:21]([C:14]1[N:13]=[C:12]([C:10]2[CH:9]=[N:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:26])([CH3:25])[CH3:1])[CH:11]=2)[N:17]2[CH:18]=[CH:19][N:20]=[C:16]2[CH:15]=1)=[O:22])(=[O:39])[CH3:38]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 20 mL flask, 5-(1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carbohydrazide (45.1 mg, 0.121 mmol) was dissolved in DCM (604 μL, 0.121 mmol). After cooling to 0° C., triethylamine (20.2 μL, 0.145 mmol) and acetyl chloride (9.45 μL, 0.133 mmol) were added. The reaction mixture was allowed to warm to ambient temperature for 15 hours. This was then diluted in EtOAc and washed with water and brine. The organic layer was then dried with MgSO4, filtered and concentrated down to afford N′-acetyl-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carbohydrazide (40.9 mg, 81.5% yield) as a light yellow solid. MS (apci) m/z=416.2 (M+H).

Workup

temperatureto warm to ambient temperature for 15 hours
washwashed with water and brine
dry with materialThe organic layer was then dried with MgSO4
filtrationfiltered
concentrationconcentrated down

Sources & evidence

ORD record: ord-88e3cf3a697a4958909b70d115ca9c3d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962596B2

Reaction notes

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