Triethylamine → HCID 25122351, compound

HRID 1664695Notes

Reaction equation

HRID 1664695 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[S:11][CH:12]=[C:13]([C@H:15]3[CH2:20][CH2:19][CH2:18][CH2:17][NH:16]3)[N:14]=2)[CH:5]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[O:38]([CH2:45][C:46](Cl)=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>ClCCl>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[S:11][CH:12]=[C:13]([C@H:15]3[CH2:20][CH2:19][CH2:18][CH2:17][N:16]3[C:46](=[O:47])[CH2:45][O:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:14]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 69703Phenoxyacetyl chlorideHCID 67357261HCID 67357261, compound

Product 1

HCID 25122351HCID 25122351, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-((R)-4-piperidin-2-yl-thiazol-2-yl)-benzoic acid methyl ester (0.048 g, 0.16 mmol) in dry dichloromethane (2 mL) under argon was treated with triethylamine (0.064 g, 0.09 ml.), dimethylaminopyridine (0.002 g, 0.020 mmol) and phenoxyacetyl chloride (0.027 g, 0.16 mmol). The mixture was stirred at room temperature for 4 h. The mixture was washed with water and saturated sodium chloride. The organic phase was dried over sodium sulphate and evaporated. The residual oil was purified by preparative HPLC: Column: YMC-Pack Pro C18 RS, 20×50 mm, S-5 um, 8 nm, No200504707(W); Gradient: 0-0.4 min: 30% acetonitrile in (water+0.1% HCO2H), 0.4-2.4 min: increse of acetonitrile fraction from 30% to 95%, 2.4-4.7 min: 95% acetonitrile, 4.7-4.8 min: decrease of acetonitrile fraction from 95% to 30%; Program end at 4.87 min; Flow: 30 ml/min. 3-{4-[(R)-1-(2-Phenoxy-acetyl)-piperidin-2-yl]-thiazol-2-yl}-benzoic acid methyl ester was obtained after lyophilization as a light yellow oil (0.033 g, 48%), MS (ISP): 437.3 (M+H)+..

Workup

  1. washThe mixture was washed with water and saturated sodium chloride
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated
  4. customThe residual oil was purified by preparative HPLC
  5. custom0-0.4 min
  6. customin (water+0.1% HCO2H), 0.4-2.4 min
  7. customfrom 30% to 95%, 2.4-4.7 min
  8. custom95% acetonitrile, 4.7-4.8 min
  9. waitProgram end at 4.87 min

Sources & evidence

ORD record
ord-5390b457eab9477a8bdb62a1a22e59b4
Source dataset
uspto-grants-2011_10
Patent number
US08039487B2

Reaction notes

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