Ethanolamine → N-[2-[(3S)-3-[(2-Hydroxyethyl)amino]-1-pyrrolidinyl]-6-methyl-5-quinolinyl]-cyclohexaneacetamide

HRID 2217889Notes

Reaction equation

HRID 2217889 reaction equation
[CH3:1][C:2]1[C:3]([NH:22][C:23](=[O:31])[CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@@H:14](OS(C)(=O)=O)[CH2:13]1)[CH:6]=[CH:5]2.[NH2:32][CH2:33][CH2:34][OH:35]>C(#N)C>[OH:35][CH2:34][CH2:33][NH:32][C@H:14]1[CH2:15][CH2:16][N:12]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[C:3]=3[NH:22][C:23](=[O:31])[CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[N:8]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 86609748HCID 86609748, compound

Product 1

HCID 11235257N-[2-[(3S)-3-[(2-Hydroxyethyl)amino]-1-pyrrolidinyl]-6-methyl-5-quinolinyl]-cyclohexaneacetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared according to the method of example 33(b), using N-[6-methyl-2-[(3R)-3-[(methylsulfonyl)oxy]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide (Example 86(a)) (0.16 g), 2-amino-ethanol (0.065 mL), and acetonitrile (4 mL). Purification (SiO2, 7M ammonia in methanol:methanol:dichloromethane 1:2:99 as eluant) gave the title compound (0.06 g).

Workup

  1. customPrepared
  2. customPurification (SiO2, 7M ammonia in methanol:methanol:dichloromethane 1:2:99 as eluant)

Sources & evidence

ORD record
ord-ed072c71a0ac467793eef89667076807
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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