Trifluoroacetic acid → HCID 14810833, compound

HRID 2248597Notes

Reaction equation

HRID 2248597 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[N:15]=[C:14]([CH2:16][NH:17]C(OC(C)(C)C)=O)[O:13][N:12]=2)=[CH:3]1.[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28]>C(Cl)Cl>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[N:15]=[C:14]([CH2:16][NH2:17])[O:13][N:12]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 14810827Carbamic acid, [[3-(1-methyl-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 14810833HCID 14810833, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Methyl-3-[5-t-butoxycarbonylaminomethyl-1,2,4-oxadiazol-3-yl]indole (300mg) was dissolved in CH2Cl2 (10 ml) at 0° C., trifluoroacetic acid (0.5 ml) was then added and the reaction mixture allowed to warm to room temperature over 30 mins. The reaction mixture was stirred at room temperature for twelve hours before evaporation at reduced pressure. The residue was recrystallised from cold CH2Cl2 to afford white crystals (150 mg) mp 178° C.; Found C, 48.74; H, 3.74; N 15.97 C14H13N4O3F3 requires C, 49.13; H, 3.83; N, 16.37%; δH (360 MHz, DMSO), 3.92 (3 H, s, NMe), 4.58 (2 H, s, CH2N), 7.24-7.35 (2 H, m, H-5, H-6), 7.60 (1 H, d, J=7, H-4), 8.07 (1 H, d, J=7, H-7), 8.10 (1 H, s, H-2); M/Z 228 (M+, free base 70%), 171(100), 156(80).

Workup

  1. customThe residue was recrystallised from cold CH2Cl2

Sources & evidence

ORD record
ord-0e7c56ebdb43431e8a5b8ac1baf6b218
Source dataset
uspto-grants-1991_08
Patent number
US05041456

Reaction notes

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