Triethylamine → HCID 117843478, compound

HRID 2209212Notes

Reaction equation

HRID 2209212 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].FC(F)(F)C(O)=O.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:31]2[N:32]=[C:33]([O:40][C@@H:41]([C@H:43]3[CH2:47][NH:46][C:45](=[O:48])[CH2:44]3)[CH3:42])[C:34]3[N:35]([N:37]=[CH:38][CH:39]=3)[CH:36]=2)[CH:22]=[CH:23][C:24]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(N(CC)CC)C>ClCCl>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:31]2[N:32]=[C:33]([O:40][C@@H:41]([C@H:43]3[CH2:47][NH:46][C:45](=[O:48])[CH2:44]3)[CH3:42])[C:34]3[N:35]([N:37]=[CH:38][CH:39]=3)[CH:36]=2)[CH:22]=[CH:23][C:24]=1[N:25]1[CH2:26][CH2:27][N:28]([S:2]([CH3:1])(=[O:5])=[O:3])[CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 117843901HCID 117843901, compound

Product 1

HCID 117843478HCID 117843478, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic anhydride (9.5 mg, 0.05 mmol) was added to a solution of (R)-4-((R)-1-(6-(3-methoxy-4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrazin-4-yloxy)ethyl)pyrrolidin-2-one 2,2,2-trifluoroacetate 5.48 (22.4 mg, 0.04 mmol) and triethylamine (0.05 mL, 0.36 mmol) in dichloromethane (1.8 mL). After two hours, reaction mixture was loaded directly onto silica and purified (0-8% methanol/dichloromethane) to yield (R)-4-((R)-1-((6-(3-methoxy-4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one 5.50 (19 mg).

Workup

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

Sources & evidence

ORD record
ord-64a310146b1d4653b500bafa1508fcc0
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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