Ethanolamine → HCID 68781601, compound

HRID 2264500Notes

Reaction equation

HRID 2264500 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[C:19](Cl)[N:18]=[C:17]([O:22][CH3:23])[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[NH2:33][CH2:34][CH2:35][OH:36]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[C:19]([NH:33][CH2:34][CH2:35][OH:36])[N:18]=[C:17]([O:22][CH3:23])[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 86615299HCID 86615299, compound

Product 1

HCID 68781601HCID 68781601, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 4-(4-chloro-6-methoxy-[1,3,5]triazin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (1.03 g, 3.0 mmol, 1.0 equiv) in acetonitrile (45 mL) was added N-ethyl diisopropylamine (1.56 mL, 1.18 g, 9.0 mmol, 3.0 equiv) at rt, followed by 2-amino-ethanol (0.36 mL, 0.37 g, 6.0 mmol, 2.0 equiv). The reaction mixture was heated to 50° C. for 3.5 h, then poured into crashed ice and extracted twice with ethyl acetate. The combined organic layers were washed with brine and water, then dried over MgSO4, filtered and concentrated by evaporation under reduced pressure. The crude product was purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol to give 1.00 g (90%) of the title compound as colorless foam. MS (ISP): 369.1 [M+H]+.

Workup

  1. additionpoured
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe crude product was purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol

Sources & evidence

ORD record
ord-840f5639c2f94b6dae52e1bf55a41d29
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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