Ammonium formate → HCID 90409398, compound

HRID 2177640Notes

Reaction equation

HRID 2177640 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:15]([CH3:17])=[CH:14][N:13]([CH2:18][C:19]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)([OH:21])[CH3:20])[CH:12]([CH3:30])[C:11]=3[N:10]=[N:9]2)=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]([CH3:17])[CH2:14][N:13]([CH2:18][C:19]([C:22]4[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=4)([OH:21])[CH3:20])[CH:12]([CH3:30])[C:11]=3[N:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 90408565HCID 90408565, compound

Product 1

HCID 90409398HCID 90409398, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the product of Example 238, Step 2 (200 mg, 0.49 mmol) in MeOH (2 mL) was added Pd/C (52 mg, 0.049 mmol) and ammonium formate (93 mg, 1.45 mmol). The reaction vessel was sealed and heated 80° C. for 16 h. The reaction mixture was then filtered through Celite, concentrated and purified on silica gel with 0-2% NH3 MeOH/CH2Cl2 to afford the title compound (93 mg, 46%). MS (ESI) mass calcd. C23H27FN4O2, 410.2. m/z found, 411.20 [M+H]+.

Workup

  1. customThe reaction vessel was sealed
  2. filtrationThe reaction mixture was then filtered through Celite
  3. concentrationconcentrated
  4. custompurified on silica gel with 0-2% NH3 MeOH/CH2Cl2

Sources & evidence

ORD record
ord-7010681061e3400facc38e6cc2779fae
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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