Trifluoroacetic acid → HCID 74767794, compound

HRID 629803Notes

Reaction equation

HRID 629803 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[C:17]([CH:25]3[CH2:30][CH2:29][N:28]([C:31]4[C:32]5[CH2:39][CH2:38][N:37](CC6C=CC(OC)=CC=6)[C:33]=5[N:34]=[CH:35][N:36]=4)[CH2:27][CH2:26]3)[N:18]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[CH:19]=2)=[CH:11][C:10]=1[C:49]([F:52])([F:51])[F:50].FC(F)(F)C(O)=O>>[N:34]1[C:33]2[NH:37][CH2:38][CH2:39][C:32]=2[C:31]([N:28]2[CH2:27][CH2:26][CH:25]([C:17]3[N:18]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[CH:19]=[C:15]([C:12]4[CH:13]=[CH:14][C:9]([F:8])=[C:10]([C:49]([F:50])([F:51])[F:52])[CH:11]=4)[N:16]=3)[CH2:30][CH2:29]2)=[N:36][CH:35]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90159260HCID 90159260, compound

Product 1

HCID 74767794HCID 74767794, compoundYield 99.3%

Conditions

Temperature
80 °C

Procedure

To [2-(4-(4-fluoro-3-trifluoromethyl-phenyl)-2-{1-[7-(4-methoxy-benzyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-imidazol-1-yl)-ethyl]-dimethyl-amine trifluoroacetate (50.0 mg; 0.07 mmol; 1.0 eq.) in a seal tube was added trifluoroacetic acid (1.0 ml). The reaction mixture was stirred at 80° C. for 14 hours. LC-MS showed clean reaction with 99% purity by HPLC. After Removal of TFA, the residue was dissolved in small amount of acetonitrile, added water and then lyophilized to afford the title compound as off-white solid (35 mg, 70% yield); LC-MS (M+H=504, obsd.=504);

Workup

  1. customreaction with 99% purity by HPLC
  2. customAfter Removal of TFA
  3. dissolutionthe residue was dissolved in small amount of acetonitrile
  4. additionadded water

Sources & evidence

ORD record
ord-38f0e7b3113046e693f6a3a08be26507
Source dataset
uspto-grants-2016_04
Patent number
US09315517B2

Reaction notes

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