Methyl iodide → HCID 178436412, compound

HRID 2099751Notes

Reaction equation

HRID 2099751 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:40](=O)([O-])[O-].[Na+].[Na+].IC>CS(C)=O.O>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:13][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])[C:15]2[N:16]([CH3:40])[N:17]=[N:18][N:19]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[C:8]2[CH3:12])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 178436413HCID 178436413, compound

Product 1

HCID 178436412HCID 178436412, 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 (50 mg, 0.1 mmol, 1.0 equiv), sodium carbonate (40.0 mg, 3.0 equiv), and iodomethane (24 μL, 3.0 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 the title compound. 1H-NMR (CD3OD) δ 1.30 (m, 4H), 1.57 (m, 3H), 2.50 (s, 3H), 2.75-2.95 (m, 5H), 3.40 (m, 2H), 3.68 (m, 3H), 4.05-4.40 (m, 6H), 5.35 (m, 1H), 6.75 (m, 1H), 6.95 (dd, J=7.3, 7.6, 1H), 6.98 (s, 1H), 7.12 (m, 2H), 7.35 (s, 1H). Mass spec.: 543.42 (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

Sources & evidence

ORD record
ord-5bcf09c8871444e08f727bf2a7bb56fe
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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