Diisopropylethylamine → (1R)-2-{[6-({4-[4-(cyclopentylsulfonyl)phenyl]but-3-ynyl}oxy)hexyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

HRID 2118330Notes

Reaction equation

HRID 2118330 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1.[NH2:27][CH2:28][C@@H:29]([C:31]1[CH:42]=[CH:41][C:34]2[O:35][C:36]([CH3:40])([CH3:39])[O:37][CH2:38][C:33]=2[CH:32]=1)[OH:30].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH:22]1([S:19]([C:16]2[CH:17]=[CH:18][C:13]([C:12]#[C:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:27][CH2:28][C@@H:29]([C:31]3[CH:42]=[CH:41][C:34]4[O:35][C:36]([CH3:39])([CH3:40])[O:37][CH2:38][C:33]=4[CH:32]=3)[OH:30])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 56600231(1R)-2-Amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-YL)ethanolHCID 691197221-{4-[(6-Bromohexyl)oxy]but-1-ynyl}-4-(cyclopentylsulfonyl)benzene

Product 1

HCID 69119804(1R)-2-{[6-({4-[4-(cyclopentylsulfonyl)phenyl]but-3-ynyl}oxy)hexyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanolYield 34.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-{4-[(6-bromohexyl)oxy]but-1-ynyl}-4-(cyclopentylsulfonyl) benzene (280 mg) in DMF (10 ml) were added (1R)-2-amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (WO 0266422 A1) (170 mg) and diisopropylethylamine (165 μl). The mixture was heated at 50° for 22 h before being allowed to cool to room temperature. The mixture was dissolved in EtOAC, washed with brine, dried (MgSO4) and evaporated to dryness. The residual oil was purified on a silica bond elut SPE cartridge (10 g), gradient 0% to 30% [MeOH-aqueous ammonia (10:1)] in DCM (Gradmaster™). The appropriate fractions were evaporated to give the title compound (127 mg) LCMS RT=2.87 min

Workup

  1. temperatureThe mixture was heated at 50° for 22 h
  2. dissolutionThe mixture was dissolved in EtOAC
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe residual oil was purified on a silica bond
  7. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-4614ae717199451fa1ffa593bc1325cd
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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