Trifluoroacetic acid → HCID 44180313, compound

HRID 564631Notes

Reaction equation

HRID 564631 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:60][CH3:61])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([C:29]([NH:31][CH2:32][C:33]4[CH:34]=[C:35]([C:39]5[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][N:46]6[CH2:51][CH2:50][N:49](C(OC(C)(C)C)=O)[C@@H:48]([CH3:59])[CH2:47]6)[CH:40]=5)[CH:36]=[CH:37][CH:38]=4)=[O:30])[CH:26]=[CH:27][CH:28]=3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:60][CH3:61])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([NH:31][CH2:32][C:33]4[CH:34]=[C:35]([C:39]5[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][N:46]6[CH2:51][CH2:50][NH:49][C@@H:48]([CH3:59])[CH2:47]6)[CH:40]=5)[CH:36]=[CH:37][CH:38]=4)=[O:30])[CH:24]=3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57813379HCID 57813379, compound

Product 1

HCID 44180313HCID 44180313, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,1-dimethylethyl (2S)-4-[(3′-{[({3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]phenyl}-carbonyl)amino]methyl}-3-biphenylyl)methyl]-2-methyl-1-piperazinecarboxylate (33 mg), TFA (0.2 mL) and DCM (1.0 mL) was stirred at room temperature overnight. Then TEA (0.4 mL) was added at −78° C. and the solution was then concentrated. Dilution with MeOH (0.5 mL) followed by separation via a Gilson HPLC (basic conditions) afforded the desired product (13 mg). LC-MS m/z 729 (M+H)+.

Workup

  1. concentrationthe solution was then concentrated
  2. customDilution with MeOH (0.5 mL) followed by separation via a Gilson HPLC (basic conditions)

Sources & evidence

ORD record
ord-4997512ef5f246f3a5a5105edd7894e6
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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