Trifluoroacetic acid → HCID 9915103, compound

HRID 2298425Notes

Reaction equation

HRID 2298425 reaction equation
C(OC([N:8]([CH:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)[C:9]([C:11]1[N:12]=[C:13]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=2)[N:14]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C@H:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH3:24])[N:17]=2)[CH:15]=1)=[O:10])=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[NH:44]1[CH2:43][CH2:42][CH:41]([NH:8][C:9]([C:11]2[N:12]=[C:13]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:40])[F:39])[CH:32]=3)[N:14]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C@H:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH3:24])[N:17]=3)[CH:15]=2)=[O:10])[CH2:46][CH2:45]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70157631HCID 70157631, compound

Product 1

HCID 9915103HCID 9915103, compoundYield 55.4%

Conditions

Temperature
0 °C

Procedure

(S)-1-[2-(1-Phenyl-ethylamino)-pyrimidin-4-yl]-2-(3-trifluoromethyl-phenyl)-1H-imidazole-4-carboxylic acid-N-t-butoxycarbonylpiperidin-4-ylamide (600 mg) was dissolved in 10 mL CH2Cl12 and cooled to 0° C. before adding 3 mL TFA. The reaction was allowed to warm to room temperature and stirred for 1 h. Concentration and prep HPLC on a Delta-Pak™ 40 mm×200 mm C8 column from 100/0 H2O/CH3CN to 5/95 H2O/CH3CN over 30 min yielded 280 mg of the title compound after lyophilization as a granular solid.

Workup

  1. temperatureto warm to room temperature
  2. concentrationConcentration and prep HPLC on a Delta-Pak™ 40 mm×200 mm C8 column from 100/0 H2O/CH3CN to 5/95 H2O/CH3CN over 30 min

Sources & evidence

ORD record
ord-4b8de6aabbf741bd915436877a2ad69f
Source dataset
uspto-grants-2002_12
Patent number
US06492516B1

Reaction notes

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