Ammonium formate → HCID 9819448, compound

HRID 538663Notes

Reaction equation

HRID 538663 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][N:15]([CH:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO>[C:16]1([N:15]([CH:22]2[CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23]2)[CH2:14][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 22087106HCID 22087106, compound

Product 1

HCID 9819448HCID 9819448, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 15 (1.5 g, 3.79 mmol) in methanol (50 mL) was purged with argon for 20 minutes. Ammonium formate (2.33 g, 37.87 mmol) was then added and the solution was purged for another 10 minutes. Pd—C (10%; 216 mg) was added and the reaction mixture was heated at reflux for 3 hours. The reaction mixture was filtered through the Celite® reagent and washed with methanol. The filtrate was concentrated and the crude material was purified by chromatography on 230-400 mesh silica gel eluting with 2% methanol-DCM to provide compound 16.

Workup

  1. customthe solution was purged for another 10 minutes
  2. additionPd—C (10%; 216 mg) was added
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 3 hours
  5. filtrationThe reaction mixture was filtered through the Celite® reagent
  6. washwashed with methanol
  7. concentrationThe filtrate was concentrated
  8. customthe crude material was purified by chromatography on 230-400 mesh silica gel eluting with 2% methanol-DCM

Sources & evidence

ORD record
ord-9c65c3587cdb426d88c3fe5e392668ed
Source dataset
uspto-grants-2014_10
Patent number
US08865741B2

Reaction notes

Loading…