Diisopropylethylamine → HCID 68624315, compound

HRID 2061508Notes

Reaction equation

HRID 2061508 reaction equation
[ClH:1].[F:2][C:3]1[C:11]2[NH:10][C:9](=[O:12])[N:8]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:7]=2[CH:6]=[C:5]([CH3:19])[C:4]=1[F:20].C(N(C(C)C)CC)(C)C.[O:30]1[CH2:35][CH2:34][C:33](=O)[CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[ClH:1].[F:2][C:3]1[C:11]2[NH:10][C:9](=[O:12])[N:8]([CH:13]3[CH2:14][CH2:15][N:16]([CH:33]4[CH2:34][CH2:35][O:30][CH2:31][CH2:32]4)[CH2:17][CH2:18]3)[C:7]=2[CH:6]=[C:5]([CH3:19])[C:4]=1[F:20]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 68624356HCID 68624356, compound

Product 1

HCID 68624315HCID 68624315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,5-Difluoro-6-methyl-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride D23 (120 mg) was dissolved in dichloromethane (5 ml) and diisopropylethylamine (0.2 ml, 1.2 mmol), tetrahydro-4H-pyran-4-one (0.2 ml, 2.0 mmol) and sodium triacetoxyborohydride (250 mg, 1.2 mmol) were added and the mixture stirred at room temperature for 4 h. The mixture was partitioned with water/MDC at pH9. Drying (MgSO4), evaporation, and crystallisation of the residue from diethyl ether, washing with dichloromethane gave the title compound free base, which was converted to the hydrochloride. Trituration with diethyl ether gave 35 mg of hydrochloride salt. MH+=352,

Workup

  1. customThe mixture was partitioned with water/MDC at pH9
  2. customDrying
  3. custom(MgSO4), evaporation, and crystallisation of the residue from diethyl ether
  4. washwashing with dichloromethane

Sources & evidence

ORD record
ord-53e0c35df8914548983b903c45b352b7
Source dataset
uspto-grants-2012_10
Patent number
US08283364B2

Reaction notes

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