Trifluoroacetic acid → HCID 21249883, compound

HRID 1532380Notes

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-eca22589aaaa4320a2dd08b59547ece2
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200957B1

Reaction notes

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