Ethanolamine → HCID 86677763, compound

HRID 1499840Notes

Reaction equation

HRID 1499840 reaction equation
[Cl:1][C:2]1[C:3]([CH3:30])=[C:4]([C:23]2[CH:24]=[N:25][C:26](F)=[CH:27][CH:28]=2)[C:5]([O:21][CH3:22])=[C:6]([CH:8]([N:10]2[C:14]3=[N:15][CH:16]=[N:17][C:18]([NH2:19])=[C:13]3[C:12]([CH3:20])=[N:11]2)[CH3:9])[CH:7]=1.[CH2:31]([CH2:33][NH2:34])[OH:32]>C(O)CCC>[NH2:19][C:18]1[N:17]=[CH:16][N:15]=[C:14]2[N:10]([CH:8]([C:6]3[C:5]([O:21][CH3:22])=[C:4]([C:23]4[CH:28]=[CH:27][C:26]([NH:34][CH2:33][CH2:31][OH:32])=[N:25][CH:24]=4)[C:3]([CH3:30])=[C:2]([Cl:1])[CH:7]=3)[CH3:9])[N:11]=[C:12]([CH3:20])[C:13]=12

Participants

4

Reactant 2

HCID 700EthanolamineHCID 86677764HCID 86677764, compound

Product 1

HCID 86677763HCID 86677763, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 1-{1-[5-chloro-3-(6-fluoropyridin-3-yl)-2-methoxy-4-methylphenyl]ethyl}-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (10 mg, 0.023 mmol) and ethanolamine (0.10 mL) in 1-butanol (1 mL) was stirred at 130° C. for 5 h. The crude was purified using RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product (1.6 mg, 15%). The product was isolated as a single enantiomer. LCMS calculated for C23H27ClN7O2 (M+H)+: m/z=468.2; Found: 468.2.

Workup

  1. customThe crude was purified
  2. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-7636c4f6aee545cb9253fea20e13d208
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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