Ethyl Acetate → (R)-N-(2,2-Dimethoxyethyl)-N-(hexan-2-yl)-3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanamide

HRID 909941Notes

Reaction equation

HRID 909941 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]([OH:17])=O)[CH:4]=[N:3]1.[CH3:21][O:22][CH:23]([O:32][CH3:33])[CH2:24][NH:25][C@@H:26]([CH2:28][CH2:29][CH2:30][CH3:31])[CH3:27].C(OCC)(=O)C>CCCC(C)C>[CH3:21][O:22][CH:23]([O:32][CH3:33])[CH2:24][N:25]([C@@H:26]([CH2:28][CH2:29][CH2:30][CH3:31])[CH3:27])[C:15](=[O:17])[CH2:14][CH2:13][O:12][CH2:11][CH2:10][C:9]1[CH:18]=[CH:19][CH:20]=[C:7]([C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 59224574(R)-N-(2,2-Dimethoxyethyl)hexan-2-amineHCID 592904613-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid

Product 1

HCID 59290364(R)-N-(2,2-Dimethoxyethyl)-N-(hexan-2-yl)-3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanamide

Reagents, catalysts & solvents 1

HCID 78922-MethylpentaneSolvent

Procedure

The subtitled compound (234 mg) was prepared using a similar method to that described in Preparation 3 Step iii) from 3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid [Example 2a, Step i)] and (R)—N-(2,2-dimethoxyethyl)hexan-2-amine [Preparation 13] and the reaction mixture was stirred for 2 h. The elution gradient used was 30-50% ethyl acetate in isohexane. 1H NMR (400 MHz, CDCl3) δ 7.75 (s, 1H), 7.62 (s, 1H), 7.36-7.24 (m, 3H), 7.11-7.05 (m, 1H), 4.69-4.63 and 4.41-4.37 (m, 1H), 4.38-4.31 and 3.85-3.76 (m, 1H), 3.94 (s, 3H), 3.85-3.76 (m, 2H), 3.74-3.65 (m, 2H), 3.43-3.37 (m, 6H), 3.33-3.25 (m, 1H), 3.22-3.14 (m, 1H), 2.94-2.85 (m, 2H), 2.80-2.57 (m, 2H), 1.59-1.12 (m, 9H), 0.93-0.85 (m, 3H); a ˜1:1 mixture of rotamers is observed.

Workup

  1. additiona ˜1:1 mixture of rotamers

Sources & evidence

ORD record
ord-8cbc6fb984bd48cfb178e5fb48a24b47
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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