N-Acetylhomopiperazine → HCID 44250829, compound

HRID 1409192Notes

Reaction equation

HRID 1409192 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH:11]3C[CH2:12]3)[CH:10]=[C:6]2[N:5]=[C:4]([NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)[CH:3]=1.[C:27]([N:30]1[CH2:36][CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])[CH3:28]>CN1C(=O)CCC1>[C:27]([N:30]1[CH2:36][CH2:35][CH2:34][N:33]([C:2]2[N:7]3[N:8]=[C:9]([CH2:11][CH3:12])[CH:10]=[C:6]3[N:5]=[C:4]([NH:14][C:15](=[O:26])[C:16]3[CH:21]=[CH:20][C:19]([C:22]([OH:25])([CH3:23])[CH3:24])=[CH:18][CH:17]=3)[CH:3]=2)[CH2:32][CH2:31]1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 4186202N-AcetylhomopiperazineHCID 86652274HCID 86652274, compound

Product 1

HCID 44250829HCID 44250829, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 2 mL microwave vial was placed N-(7-chloro-2-cyclopropylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2H, 75 mg, 0.21 mmol) and N-acetylhomopiperazine (59 mg, 0.42 mmol). To the sealed vial was then added NMP (2 ml) and the mixture was then heated in the microwave at 120° C. for 30 minutes. After cooling to room temperature, the reaction mixture was partitioned between brine and EtOAc. The aqueous layer was extracted once more with EtOAc, and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by recrystallization from ether and EtOAc to give the titled compound (50 mg, 51% yield) as an off-white solid. ESI-MS: m/z 465 (M+H)+.

Workup

  1. customthe reaction mixture was partitioned between brine and EtOAc
  2. extractionThe aqueous layer was extracted once more with EtOAc
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by recrystallization from ether and EtOAc

Sources & evidence

ORD record
ord-7fcf27f16e5648928170d30f212000b7
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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