2-Chloroethanol → RQ-00202730

HRID 241671Notes

Reaction equation

HRID 241671 reaction equation
[NH:1]1[CH2:4][CH:3]([S:5]([C:8]2[CH:26]=[CH:25][C:11]3[N:12]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[C:13]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:14][C:10]=3[CH:9]=2)(=[O:7])=[O:6])[CH2:2]1.C(N(CC)CC)C.Cl[CH2:35][CH2:36][OH:37]>O>[CH3:23][N:22]([CH3:24])[CH2:21][CH2:20][N:12]1[C:11]2[CH:25]=[CH:26][C:8]([S:5]([CH:3]3[CH2:4][N:1]([CH2:35][CH2:36][OH:37])[CH2:2]3)(=[O:6])=[O:7])=[CH:9][C:10]=2[N:14]=[C:13]1[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 8471TriethylamineHCID 58513578HCID 58513578, compound

Product 1

HCID 46852212RQ-00202730Yield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(5-(azetidin-3-ylsulfonyl)-2-neopentyl-1H-benzo[d]imidazol-1-yl)-N,N-dimethylethanamine (prepared in STEP A of Example 22, 554 mg, 1.46 mmol), triethylamine (226 microL, 1.61 mmol) and 2-chloroethanol (3.53 g, 43.9 mmol) was stirred at 60° C. for 9 h. The resulting mixture was diluted with water (30 mL) and extracted with dichloromethane (50 mL×3). The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude product was purified by reverse phase HPLC (0.4% aqueous ammonia-acetonitrile=96:4 to 4:96) to give the title compound (238 mg, 39%) as a clear grease.

Workup

  1. extractionextracted with dichloromethane (50 mL×3)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by reverse phase HPLC (0.4% aqueous ammonia-acetonitrile=96:4 to 4:96)

Sources & evidence

ORD record
ord-df9dad78dc2c475b927ac00406eee832
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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