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

HRID 1852999
Notes
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Reaction equation

HRID 1852999 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 674592615-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carbohydrazide

Product 1

HCID 67459049N'-acetyl-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carbohydrazideYield 81.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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

  1. temperatureto warm to ambient temperature for 15 hours
  2. washwashed with water and brine
  3. dry with materialThe organic layer was then dried with MgSO4
  4. filtrationfiltered
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes