Ammonium formate → HCID 178515402, compound

HRID 1951293Notes

Reaction equation

HRID 1951293 reaction equation
C([O:4][C:5]1[CH:38]=[C:8]2[N:9]=[CH:10][CH:11]=[C:12]([S:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]([C:31]5[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=5)=[N:23][N:22]=4)=[CH:16][CH:15]=3)[N:7]2[N:6]=1)C=C.C([O-])=O.[NH4+]>CO.[Pd].CCOC(C)=O>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21]([NH:20][C:17]3[CH:16]=[CH:15][C:14]([S:13][C:12]4[N:7]5[N:6]=[C:5]([OH:4])[CH:38]=[C:8]5[N:9]=[CH:10][CH:11]=4)=[CH:19][CH:18]=3)=[N:22][N:23]=2)=[CH:32][CH:33]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 44232576HCID 44232576, compound

Product 1

HCID 178515402HCID 178515402, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of N-(4-(2-(allyloxy)pyrazolo[1,5-a]pyrimidin-7-ylthio)phenyl)-4-(4-chlorophenyl)phthalazin-1-amine (0.110 g, 0.20 mmol, Example 4) and ammonium formate (130 mg, 2.0 mmol) in MeOH (7 mL) was added a slurry of 10% palladium on carbon, (44 mg) in EtOAc (1 mL). The mixture was heated to 65° C. After 8 hrs, the mixture was cooled to RT, filtered over celite, concentrated in vacuo, and purified by silica gel chromatography using 5-15% MeOH in CH2Cl2 with 1% NH4OH to afford 7-(4-(4-(4-chlorophenyl)phthalazin-1-ylamino)phenylthio)pyrazolo[1,5-a]pyrimidin-2-ol as a light yellow solid. MS: Found M+H+=497.0.

Workup

  1. temperaturethe mixture was cooled to RT
  2. filtrationfiltered over celite
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-d947be2f7f1845c1a187dba9e7cb4099
Source dataset
uspto-grants-2013_03
Patent number
US08404694B2

Reaction notes

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