N-(6-chloro-8-nitro-9H-beta-carbolin-4-yl)-2,2,2-trifluoro-acetamide → N-(8-amino-6-chloro-9H-beta-carbolin-4-yl)-2,2,2-trifluoro-acetamide

HRID 552214Notes

Reaction equation

HRID 552214 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:15]([O-])=O)[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[C:5]2=1>CO>[NH2:15][C:13]1[CH:14]=[C:2]([Cl:1])[CH:3]=[C:4]2[C:12]=1[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[C:5]2=1

Participants

3

Reactant 1

HCID 86595094N-(6-chloro-8-nitro-9H-beta-carbolin-4-yl)-2,2,2-trifluoro-acetamide

Product 1

HCID 86595095N-(8-amino-6-chloro-9H-beta-carbolin-4-yl)-2,2,2-trifluoro-acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude N-(6-chloro-8-nitro-9H-β-carbolin-4-yl)-2,2,2-trifluoro-acetamide (130 mg, 0.36 mmol) was dissolved in 7 ml of MeOH and the reaction vessel was vacuum purged 3× with N2. Platinum (20 mg, 20% wt. on activated carbon) was added quickly, and the reaction vessel was again vacuum purged 3× with N2, followed by 3 additional vacuum purge cycles with H2. The reaction was allowed to stir under H2 at 1 atm overnight. Upon completion, the reaction vessel was purged of H2 and filtered over celite. The celite was washed several times with methanol until the filtrates were clear. The combined filtrates were concentrated to give N-(8-amino-6-chloro-9H-β-carbolin-4-yl)-2,2,2-trifluoro-acetamide as a yellow solid (112 mg, 95%). 1H-NMR (300 MHz, DMSO-d6): δ 11.83 (s, 1H), 8.98 (s, 1H), 8.30 (s, 1H), 7.10 (s, 1H), 6.82 (s, 1H), 5.87 (br, 2H). Formic acid standard conditions. DAD RT=1.95 min. M+H=329.

Workup

  1. custompurged 3× with N2
  2. additionPlatinum (20 mg, 20% wt. on activated carbon) was added quickly
  3. custompurged 3× with N2
  4. custompurge cycles with H2
  5. customUpon completion, the reaction vessel was purged of H2
  6. filtrationfiltered over celite
  7. washThe celite was washed several times with methanol until the filtrates
  8. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-85182a58917246d98d03dd4c1859f27d
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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