Acetone → HCID 21925655, compound

HRID 1243594Notes

Reaction equation

HRID 1243594 reaction equation
[CH3:1][C:2]([CH3:4])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:19][C:20]1[CH:50]=[CH:49][C:23]2[N:24]3[C:28]([CH2:29][N:30]([CH:32]4[CH2:36][CH2:35][NH:34][CH2:33]4)[CH2:31][C:22]=2[CH:21]=1)=[N:27][N:26]=[C:25]3[CH:37]1[CH2:42][CH2:41][N:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=2)[CH2:39][CH2:38]1.C(=O)(O)[O-].[Na+]>ClCCl>[ClH:19].[ClH:19].[ClH:19].[Cl:19][C:20]1[CH:50]=[CH:49][C:23]2[N:24]3[C:28]([CH2:29][N:30]([CH:32]4[CH2:36][CH2:35][N:34]([CH:2]([CH3:4])[CH3:1])[CH2:33]4)[CH2:31][C:22]=2[CH:21]=1)=[N:27][N:26]=[C:25]3[CH:37]1[CH2:38][CH2:39][N:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=2)[CH2:41][CH2:42]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21925632HCID 21925632, compound

Product 1

HCID 21925655HCID 21925655, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetone (0.1 ml) and sodium triacetoxyborohydride (47 mg, 0.22 mmol) were added to a solution of the amine from example 56 (100 mg, 0.22 mmol) in dichloromethane (5 ml), and the reaction mixture was stirred at room temperature for 16 hours. Saturated aqueous sodium bicarbonate solution (10 ml) was added, the mixture was stirred vigorously for 10 minutes, and the layers were separated. The organic layer was evaporated under reduced pressure and the residue purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (95:5:0.5) as eluant. The product was treated with ethereal hydrochloric acid to afford the title compound.

Workup

  1. stirringthe mixture was stirred vigorously for 10 minutes
  2. customthe layers were separated
  3. customThe organic layer was evaporated under reduced pressure
  4. customthe residue purified by column chromatography on silica gel
  5. additionThe product was treated with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-454a8c26cc0e44aabc1060bc99a313a5
Source dataset
uspto-grants-2006_10
Patent number
US07119088B2

Reaction notes

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