Triethylamine → HCID 117843446, compound

HRID 2209209Notes

Reaction equation

HRID 2209209 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].FC(F)(F)C(O)=O.[N:17]1([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[N:30]=[C:31]([O:38][C@@H:39]([C@H:41]4[CH2:45][NH:44][C:43](=[O:46])[CH2:42]4)[CH3:40])[C:32]4[N:33]([N:35]=[CH:36][CH:37]=4)[CH:34]=3)=[CH:25][CH:24]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([N:20]1[CH2:19][CH2:18][N:17]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[N:30]=[C:31]([O:38][C@@H:39]([C@H:41]4[CH2:45][NH:44][C:43](=[O:46])[CH2:42]4)[CH3:40])[C:32]4[N:33]([N:35]=[CH:36][CH:37]=4)[CH:34]=3)=[CH:25][CH:24]=2)[CH2:22][CH2:21]1)(=[O:5])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 117843121HCID 117843121, compound

Product 1

HCID 117843446HCID 117843446, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic anhydride (9.3 mg, 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, 0.36 mmol) in dichloromethane (1.8 mL). After two hours, reaction mixture was loaded directly onto silica gel and purified (0-8% methanol/dichloromethane) to yield (R)-4-((R)-1-((6-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one 5.46 (19.2 mg).

Workup

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

Sources & evidence

ORD record
ord-db743be3f0e049268c44065e481291f6
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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