Trifluoroacetic acid → HCID 66685785, compound

HRID 337042Notes

Reaction equation

HRID 337042 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:37])=[C:11]([N:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH2:20][C:21]4[CH:22]=[C:23]([CH2:27][NH:28]C(=O)OC(C)(C)C)[CH:24]=[CH:25][CH:26]=4)[C:14]3=[O:36])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[NH2:28][CH2:27][C:23]1[CH:22]=[C:21]([CH2:20][NH:19][C:15]2[C:14](=[O:36])[N:13]([C:11]3[CH:12]=[C:7]([CH:8]=[CH:9][C:10]=3[CH3:37])[C:5]([NH:4][CH:1]3[CH2:2][CH2:3]3)=[O:6])[CH:18]=[CH:17][N:16]=2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86669859HCID 86669859, compound

Product 1

HCID 66685785HCID 66685785, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of [[3-[[[4-[5-[(cyclopropylamino)carbonyl]-2-methylphenyl]-3,4-dihydro-3-oxopyrazinyl]amino]methyl]phenyl]methyl]-carbamic acid, 1,1-dimethylethyl ester (Example 51,90 mg), dichloromethane (2 mL) and trifluoroacetic acid (0.5 mL) was stirred at room temperature for 30 min. The mixture was concentrated in vacuo. Purification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent) afforded the title compound as a solid (22 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customPurification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent)

Sources & evidence

ORD record
ord-e014fddd654c4a4bb54bfb1ed1cd3610
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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