Formamide → HCID 22031489, compound

HRID 1792447Notes

Reaction equation

HRID 1792447 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Br:15][C:16]1[C:17]([C:40]2[CH:45]=[CH:44][C:43](N)=[CH:42][CH:41]=2)=[N:18][N:19]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=1.[CH:47]([NH2:49])=O.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C.ClCCCl>[Br:15][C:16]1[C:17]([C:40]2[CH:45]=[CH:44][C:43]([N:49]([CH3:47])[CH3:1])=[CH:42][CH:41]=2)=[N:18][N:19]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=1

Participants

8

Reactant 4

HCID 713FormamideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22032174HCID 22032174, compound

Product 1

HCID 22031489HCID 22031489, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.54 g sodium triacetoxy borohydride was added little by little at room temperature to a mixture of 1.44 g 4-(4-bromo-1-trityl-1H-pyrazol-3-yl)phenylamine (compound in Production Example 152), 0.61 mL of 37% formamide and 40 mL 1,2-dichloroethane, and the mixture was stirred for 3 days. Ethyl acetate and an aqueous saturated sodium bicarbonate solution were added to the reaction solution and stirred, then water was added thereto, and the organic layer was separated. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated, and diisopropyl ether was added to the resulting residues which were then triturated, and the crystals were collected by filtration. The crystals were dried over a vacuum pump, to give 1.18 g of the title compound as pale brown crystals.

Workup

  1. stirringstirred
  2. customthe organic layer was separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe filtrate was evaporated
  7. additiondiisopropyl ether was added to the resulting residues which
  8. customwere then triturated
  9. filtrationthe crystals were collected by filtration
  10. customThe crystals were dried over a vacuum pump

Sources & evidence

ORD record
ord-1b320b4caf48445d87272a3586e3dd76
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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