Benzyl Bromide → HCID 178436411, compound

HRID 2099752Notes

Reaction equation

HRID 2099752 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:13][CH:14]([NH:20][C:21]([N:23]2[CH2:28][CH2:27][CH:26]([N:29]3[CH2:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[NH:31][C:30]3=[O:39])[CH2:25][CH2:24]2)=[O:22])[C:15]2[NH:19][N:18]=[N:17][N:16]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[C:8]2[CH3:12])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH2:46](Br)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CS(C)=O.O>[CH2:46]([N:19]1[C:15]([CH:14]([NH:20][C:21]([N:23]2[CH2:24][CH2:25][CH:26]([N:29]3[CH2:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[NH:31][C:30]3=[O:39])[CH2:27][CH2:28]2)=[O:22])[CH2:13][C:5]2[CH:6]=[C:7]3[C:11](=[C:3]([CH2:1][CH3:2])[CH:4]=2)[NH:10][N:9]=[C:8]3[CH3:12])=[N:16][N:17]=[N:18]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 178436413HCID 178436413, compound

Product 1

HCID 178436411HCID 178436411, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carboxylic acid [2-(7-ethyl-3-methyl-1H-indazol-5-yl)-1-(1H-tetrazol-5-yl)-ethyl]-amide (30 mg, 0.05 mmol, 1.0 equiv), sodium carbonate (18.0 mg, 3.0 equiv), and benzyl bromide (8 μL, 1.1 equiv) were combined in dimethylsulfoxide and the mixture stirred at room temperature overnight. The mixture was then diluted with water and extracted with ethyl acetate (3×). The combined organic extracts were washed with water (3×), brine (3×), dried over sodium sulfate, and concentrated. Purification by preparative HPLC afforded a mixture of the two alkylated regioisomers which were not separated. LC/MS: tR=1.68 min, 619.44 (MH)+.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with water (3×), brine (3×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by preparative HPLC
  6. customafforded
  7. additiona mixture of the two alkylated regioisomers which
  8. customwere not separated

Sources & evidence

ORD record
ord-378a70bab0cb45d4951e129d0d8ac706
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

Loading…