Trifluoroacetic acid → (R)-5-(4-cyanobenzyl)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid [4-(1-pyridin-2-yl-cyclopropylcarbamoyl)-piperidin-4-yl]-amide

HRID 1040552Notes

Reaction equation

HRID 1040552 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([NH:26][C:27]([C:29]2[N:33]3[C@@:34]([CH2:47][C:48]4[CH:53]=[CH:52][C:51]([C:54]#[N:55])=[CH:50][CH:49]=4)([CH3:46])[C:35](=[O:45])[N:36]([C:37]4[CH:42]=[C:41]([Cl:43])[CH:40]=[C:39]([Cl:44])[CH:38]=4)[C:32]3=[N:31][CH:30]=2)=[O:28])([C:14](=[O:25])[NH:15][C:16]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:16]1([NH:15][C:14]([C:11]2([NH:26][C:27]([C:29]3[N:33]4[C@@:34]([CH2:47][C:48]5[CH:53]=[CH:52][C:51]([C:54]#[N:55])=[CH:50][CH:49]=5)([CH3:46])[C:35](=[O:45])[N:36]([C:37]5[CH:42]=[C:41]([Cl:43])[CH:40]=[C:39]([Cl:44])[CH:38]=5)[C:32]4=[N:31][CH:30]=3)=[O:28])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:25])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 584311224-{[(R)-5-(4-cyanobenzyl)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-4-(1-pyridin-2-yl-cyclopropyl-carbamoyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58431246(R)-5-(4-cyanobenzyl)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid [4-(1-pyridin-2-yl-cyclopropylcarbamoyl)-piperidin-4-yl]-amideYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[(R)-5-(4-cyanobenzyl)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-4-(1-pyridin-2-yl-cyclopropyl-carbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (140 mg, 0.18 mmol) in CH2Cl2 (0.5 mL) was added TFA (0.5 mL) and stirred at room temperature for 1 h. The solvent was removed in vacuo to afford (R)-5-(4-cyanobenzyl)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid [4-(1-pyridin-2-yl-cyclopropylcarbamoyl)-piperidin-4-yl]-amide as a white solid (120 mg), m/z 683.8 [M+1]+.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8ce82613752c4adbb2e478fc48c87506
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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