Trifluoroacetic acid → HCID 21249883, compound

HRID 1956534Notes

Reaction equation

C(OC(=O)[N:7]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N:19]3[N:23]=[N:22][NH:21][N:20]3[CH2:24][CH2:25][CH2:26][CH3:27])[CH:17]=2)[NH:12][C:11]=1[C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[CH:29]=1)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH2:36]([NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N:19]3[N:23]=[N:22][NH:21][N:20]3[CH2:24][CH2:25][CH2:26][CH3:27])[CH:17]=2)[NH:12][C:11]=1[C:28]1[CH:29]=[C:30]([CH3:35])[CH:31]=[C:32]([CH3:34])[CH:33]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 53691107HCID 53691107, compound

Product 1

HCID 21249883HCID 21249883, compound

Conditions

Temperature: 0 °C

Procedure

To a solution of benzyl-{2-[5-(2-butylpentazol-1-yl)-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-ethyl}carbamic acid tert-butyl ester (57 mg in 3.5 mL methylene chloride) at 0° C. was added 0.12 mL anisole followed by 0.80 mL trifluoroacetic acid and the mixture stirred at 0° C. After 1.5 hours, the mixture was concentrated in vacuo and the residual acid removed by azeotrope with toluene to give the crude title compound in quantitative yield.

Workup

concentrationthe mixture was concentrated in vacuo
customthe residual acid removed by azeotrope with toluene

Sources & evidence

ORD record: ord-03e3557da6d942ef8daa9a39c93d203e
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05780437

Reaction notes

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