Trifluoroacetic acid → methyl 1-(4-fluorobenzyl)-3-(3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamido)cyclohexanecarboxylate

HRID 530876Notes

Reaction equation

HRID 530876 reaction equation
[F:1][C:2]1[CH:56]=[CH:55][C:5]([CH2:6][C:7]2([C:51]([O:53][CH3:54])=[O:52])[CH2:12][CH2:11][CH2:10][CH:9]([NH:13][C:14]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:20]=[C:19]4[C:44]3[CH:49]=[CH:48][N:47]=[C:46]([CH3:50])[CH:45]=3)=[O:15])[CH2:8]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[F:1][C:2]1[CH:56]=[CH:55][C:5]([CH2:6][C:7]2([C:51]([O:53][CH3:54])=[O:52])[CH2:12][CH2:11][CH2:10][CH:9]([NH:13][C:14]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][N:20]=[C:19]4[C:44]3[CH:49]=[CH:48][N:47]=[C:46]([CH3:50])[CH:45]=3)=[O:15])[CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67985845methyl 1-(4-fluorobenzyl)-3-(3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamido)cyclohexanecarboxylate

Product 1

HCID 67985855methyl 1-(4-fluorobenzyl)-3-(3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamido)cyclohexanecarboxylate

Procedure

In a flask, methyl 1-(4-fluorobenzyl)-3-(3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamido)cyclohexanecarboxylate (230 mg, 0.31 mmol) was reacted with trifluoroacetic acid (3 mL) for 1 hour. After reaction completion triethylsilane (0.1 mL) was added, and the reaction was stirred for an additional 15 minutes. The reaction was concentrated and rinsed with diethyl ether. The crude product was progressed to the next step without further purification.

Workup

  1. additionwas added
  2. concentrationThe reaction was concentrated
  3. washrinsed with diethyl ether
  4. customThe crude product was progressed to the next step without further purification

Sources & evidence

ORD record
ord-c8d813e91f5349d69206a1ce63d87b7d
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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