Ammonium formate → HCID 71059696, compound

HRID 405263Notes

Reaction equation

HRID 405263 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=4)=[CH:18][C:17]=3[C:28]3[CH:29]=[CH:30][C:31]([C:34]([NH:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[O:35])=[N:32][CH:33]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH:22]1([C:19]2[CH:20]=[CH:21][C:16]([CH2:15][NH:14][C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:13][CH:12]=3)=[C:17]([C:28]3[CH:29]=[CH:30][C:31]([C:34]([NH:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[O:35])=[N:32][CH:33]=3)[CH:18]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 71060139HCID 71060139, compound

Product 1

HCID 71059696HCID 71059696, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(5-(4-(((4′-fluoro-[1,1′-biphenyl]-4-yl)amino)methyl)-2′,3′,4′,5′-tetrahydro-[1,1′-biphenyl]-3-yl)picolinamido)propanoic acid (47.6 mg, 0.087 mmol), ammonium formate (54.6 mg, 0.87 mmol) and 10% Pd—C (9.2 mg, 0.0087 mmol) in MeOH (5 mL) was refluxed for 1 h, then filtered through CELITE, washed with DCM-MeOH. The filtrate was concentrated and purified via column chromatography to give the title compound.

Workup

  1. temperaturewas refluxed for 1 h
  2. filtrationfiltered through CELITE
  3. washwashed with DCM-MeOH
  4. concentrationThe filtrate was concentrated
  5. custompurified via column chromatography

Sources & evidence

ORD record
ord-ab41e9190744449099211cc78cce4b06
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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