Trifluoroacetic acid → HCID 67389228, compound

HRID 1040546Notes

Reaction equation

HRID 1040546 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2([NH:19][C:20]([C:22]3[N:26]4[C@@:27]([CH2:40][C:41]5[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[CH:43][CH:42]=5)([CH3:39])[C:28](=[O:38])[N:29]([C:30]5[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[CH:31]=5)[C:25]4=[N:24][CH:23]=3)=[O:21])[CH2:18][CH2:17]2)=[O:15])[CH:10]([C:49]([O:51]C(C)(C)C)=[O:50])[CH2:9]1)=O)(C)(C)C.[C:56]([OH:62])([C:58]([F:61])([F:60])[F:59])=[O:57]>C(Cl)Cl>[F:59][C:58]([F:61])([F:60])[C:56]([OH:62])=[O:57].[C:47]([C:44]1[CH:45]=[CH:46][C:41]([CH2:40][C@@:27]2([CH3:39])[N:26]3[C:22]([C:20]([NH:19][C:16]4([C:14]([N:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH:10]5[C:49]([OH:51])=[O:50])=[O:15])[CH2:17][CH2:18]4)=[O:21])=[CH:23][N:24]=[C:25]3[N:29]([C:30]3[CH:31]=[C:32]([Cl:37])[CH:33]=[C:34]([Cl:36])[CH:35]=3)[C:28]2=[O:38])=[CH:42][CH:43]=1)#[N:48]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58431191HCID 58431191, compound

Product 1

HCID 67389228HCID 67389228, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(1-{[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarbonyl)-piperazine-1,3-dicarboxylic acid di-tert-butyl ester (256 mg, 0.32 mmol) was dissolved in CH2Cl2 (2 mL) and TFA (2 mL) was added dropwise. After 16 h, the reaction was concentrated in vacuo. The crude orange oil was dissolved in DMSO (1.5 mL), purified via reverse phase HPLC to afford 64 mg of 1-(1-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclo-propanecarbonyl)-piperazine-2-carboxylic acid trifluoroacetic acid salt as a white solid.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutionThe crude orange oil was dissolved in DMSO (1.5 mL)
  3. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-797ab4a02a044403ba2f14192733b769
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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