2-Amino-1-butanol, (+)- → 1-[5-Chloro-2-(1-hydroxymethyl-propylamino)-pyrimidin-4-yl]-piperidine-4-carboxylic acid [1-(3-chloro-phenyl)-2-hydroxy-ethyl]-amide

HRID 1295677Notes

Reaction equation

HRID 1295677 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:11][C:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[C:25]([Cl:26])=[CH:24][N:23]=[C:22](Cl)[N:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[NH2:28][C@@H:29]([CH2:32][CH3:33])[CH2:30][OH:31]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:11][C:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[C:25]([Cl:26])=[CH:24][N:23]=[C:22]([NH:28][CH:29]([CH2:30][OH:31])[CH2:32][CH3:33])[N:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1200842-Amino-1-butanol, (+)-HCID 866013611-(2,5-Dichloro-pyrimidin-4-yl)-piperidine-4-carboxylic acid [1-(3-chloro-phenyl)-2-hydroxy-ethyl]-amide

Product 1

HCID 866013631-[5-Chloro-2-(1-hydroxymethyl-propylamino)-pyrimidin-4-yl]-piperidine-4-carboxylic acid [1-(3-chloro-phenyl)-2-hydroxy-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2,5-Dichloro-pyrimidin-4-yl)-piperidine-4-carboxylic acid [1-(3-chloro-phenyl)-2-hydroxy-ethyl]-amide (20 mg, 0.05 mmol) was dissolved in absolute ethanol (1 mL) then (S)-2-amino-butanol (0.1 mL) was added. The mixture was heated in a sealed Teflon reaction vial at 80° C. overnight. The resulting mixture was purified by preparative TLC (1 mm silica; eluent ethyl acetate) to afford the title compound as a colorless oil (4 mg). LC/MS Rt=4.42 minutes; 483.0 (M+1); 1H NMR δ 7.88 (s, 1H) 7.26 (m, 4H) 5.21 (NH) 4.97 (m, 1H) 3.91 (dd, J=11.2, 3.8, 1H) 3.86 (dd, J=11.2, 5.8, 1H) 3.7 (m, 1H) 3.66 (m, 5H) 3.62 (m, 1H) 3.54 (m, 4H) 1.65 (m, 1H) 1.54 (m, 1H) 1.26 (OH) 0.99 (t, J=7.5, 3H).

Workup

  1. customThe resulting mixture was purified by preparative TLC (1 mm silica; eluent ethyl acetate)

Sources & evidence

ORD record
ord-4f77f3bec8284947b9bbf67553443c86
Source dataset
uspto-grants-2007_07
Patent number
US07244735B2

Reaction notes

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