Acetic Anhydride → HCID 117843733, compound

HRID 2209208Notes

Reaction equation

HRID 2209208 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].FC(F)(F)C(O)=O.[N:15]1([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:28]=[C:29]([O:36][C@@H:37]([C@H:39]4[CH2:43][NH:42][C:41](=[O:44])[CH2:40]4)[CH3:38])[C:30]4[N:31]([N:33]=[CH:34][CH:35]=4)[CH:32]=3)=[CH:23][CH:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(CC)CC)C>ClCCl>[C:1]([N:18]1[CH2:17][CH2:16][N:15]([C:21]2[CH:22]=[CH:23][C:24]([C:27]3[N:28]=[C:29]([O:36][C@@H:37]([C@H:39]4[CH2:43][NH:42][C:41](=[O:44])[CH2:40]4)[CH3:38])[C:30]4[N:31]([N:33]=[CH:34][CH:35]=4)[CH:32]=3)=[CH:25][CH:26]=2)[CH2:20][CH2:19]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 117843121HCID 117843121, compound

Product 1

HCID 117843733HCID 117843733, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (5 μl, 0.05 mmol) was added to a solution of (R)-4-((R)-1-(6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrazin-4-yloxy)ethyl)pyrrolidin-2-one 2,2,2-trifluoroacetate 5.44 (22.38 mg, 0.04 mmol) and triethylamine (0.05 mL, 0.33 mmol) in dichloromethane (1.8 mL) at room temperature. After 90 min, reaction mixture was loaded directly onto silica gel and purified (0-8% methanol/dichloromethane) to yield (R)-4-((R)-1-((6-(4-(4-acetylpiperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one 5.45 (17.1 mg).

Workup

  1. customreaction mixture
  2. custompurified (0-8% methanol/dichloromethane)

Sources & evidence

ORD record
ord-a9a076ae3afc4c2bab01679e61a3139d
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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