Ammonium formate → HCID 66689895, compound

HRID 1697406Notes

Reaction equation

HRID 1697406 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([NH:21][C:22]1[C:23](=[O:43])[N:24]([C:29]2[CH:30]=[C:31]([CH:38]=[C:39]([F:42])[C:40]=2[CH3:41])[C:32]([NH:34][CH:35]2[CH2:37][CH2:36]2)=[O:33])[CH:25]=[C:26](Br)[N:27]=1)([CH3:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH2:1]([O:8][CH2:9][CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([NH:21][C:22]1[C:23](=[O:43])[N:24]([C:29]2[CH:30]=[C:31]([CH:38]=[C:39]([F:42])[C:40]=2[CH3:41])[C:32]([NH:34][CH:35]2[CH2:37][CH2:36]2)=[O:33])[CH:25]=[CH:26][N:27]=1)([CH3:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66689585HCID 66689585, compound

Product 1

HCID 66689895HCID 66689895, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent2×

Conditions

Temperature
75 °C

Procedure

To 3-[3-{[1-(2-{[2-(Benzyloxy)ethyl]sulfanyl}phenyl)-1-methylethyl]amino}-5-bromo-2-oxopyrazin-1(2H)-yl]-N-cyclopropyl-5-fluoro-4-methylbenzamide (Example 320e, 1.7 g) in ethanol (35 mL) was added ammonium formate (2.255 g) and Pd/C (0.544 g) and the resulting solution heated at 75° C. for 1 h. After cooling to room temperature, type 490 paste 10% Pd/C (0.272 g) slurried in ethanol (5 mL) was added and the reaction heated to 75° C. for 1 hr. The reaction was filtered through celite then the filtrate concentrated in vacuo then extracted into DCM. The organic solution was dried (MgSO4) and concentrated in vacuo to give the sub title compound (1.290 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionwas added
  3. temperaturethe reaction heated to 75° C. for 1 hr
  4. filtrationThe reaction was filtered through celite
  5. concentrationthe filtrate concentrated in vacuo
  6. extractionthen extracted into DCM
  7. dry with materialThe organic solution was dried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25b9578d77aa40e68e61b339ea231b5d
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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