Acetone → HCID 21925655, compound

HRID 2118049Notes

Reaction equation

HRID 2118049 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-a6e3f67163b14e35a0ee5b152c2a1b9f
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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