Acetic Anhydride → HCID 117843269, compound

HRID 2209218Notes

Reaction equation

HRID 2209218 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].FC(F)(F)C(O)=O.[CH3:15][C:16]1[CH:17]=[N:18][N:19]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[CH:27][CH:26]=3)[N:22]=[C:21]([O:37][C@@H:38]([C@H:40]3[CH2:44][NH:43][C:42](=[O:45])[CH2:41]3)[CH3:39])[C:20]=12.C(N(CC)CC)C>ClCCl>[C:1]([N:34]1[CH2:33][CH2:32][N:31]([C:28]2[CH:29]=[CH:30][C:25]([C:23]3[N:22]=[C:21]([O:37][C@@H:38]([C@H:40]4[CH2:44][NH:43][C:42](=[O:45])[CH2:41]4)[CH3:39])[C:20]4[N:19]([N:18]=[CH:17][C:16]=4[CH3:15])[CH:24]=3)=[CH:26][CH:27]=2)[CH2:36][CH2:35]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 117843774HCID 117843774, compound

Product 1

HCID 117843269HCID 117843269, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (3.1 μL, 0.03 mmol) was added to a solution of (R)-4-((R)-1-(3-methyl-6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrazin-4-yloxy)ethyl)pyrrolidin-2-one 2,2,2-trifluoroacetate 5.56 (14.6 mg, 0.03 mmol) and triethylamine (0.03 mL, 0.21 mmol) in dichloromethane (1.5 mL) at room temperature. After two hours, reaction mixture was directly loaded onto silica gel and purified (0-10% methanol/dichloromethane) to yield (R)-4-((R)-1-((6-(4-(4-acetylpiperazin-1-yl)phenyl)-3-methylpyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one 5.57 (11 mg).

Workup

  1. customreaction mixture
  2. custompurified (0-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-0995fa0cb7324045bde21ac5ef17cbd4
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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