Acetic Anhydride → HCID 117843453, compound

HRID 2209221Notes

Reaction equation

HRID 2209221 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].FC(F)(F)C(O)=O.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:29]2[N:30]=[C:31]([O:39][C@@H:40]([C@H:42]3[CH2:46][NH:45][C:44](=[O:47])[CH2:43]3)[CH3:41])[C:32]3[N:33]([N:35]=[CH:36][C:37]=3[CH3:38])[CH:34]=2)[CH:20]=[CH:21][C:22]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)CC)C>ClCCl>[C:1]([N:26]1[CH2:25][CH2:24][N:23]([C:22]2[CH:21]=[CH:20][C:19]([C:29]3[N:30]=[C:31]([O:39][C@@H:40]([C@H:42]4[CH2:46][NH:45][C:44](=[O:47])[CH2:43]4)[CH3:41])[C:32]4[N:33]([N:35]=[CH:36][C:37]=4[CH3:38])[CH:34]=3)=[CH:18][C:17]=2[O:16][CH3:15])[CH2:28][CH2:27]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 117843751HCID 117843751, compound

Product 1

HCID 117843453HCID 117843453, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic Anhydride (4 μl, 0.04 mmol) was added to a solution of (R)-4-((R)-1-(6-(3-methoxy-4-(piperazin-1-yl)phenyl)-3-methylpyrazolo[1,5-a]pyrazin-4-yloxy)ethyl)pyrrolidin-2-one 2,2,2-trifluoroacetate 5.60 (18.1 mg, 0.03 mmol) and triethylamine (0.04 ml, 0.28 mmol) in dichloromethane (2 mL) at room temperature. After 90 min, reaction mixture was directly loaded onto silica gel and purified (0-8% methanol/dichloromethane) to yield (R)-4-((R)-1-((6-(4-(4-acetylpiperazin-1-yl)-3-methoxyphenyl)-3-methylpyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one 5.61 (13.6 mg).

Workup

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

Sources & evidence

ORD record
ord-2b76d68f36474a4995dab4dcdb969cd8
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

Loading…