Ethyl Acetate → N-Cycloheptyl-N-(2,2-dimethoxyethyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanamide

HRID 909942Notes

Reaction equation

HRID 909942 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:33][CH3:34])[CH2:24][NH:25][CH:26]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(OCC)(=O)C>CCCC(C)C>[CH:26]1([N:25]([CH2:24][CH:23]([O:33][CH3:34])[O:22][CH3:21])[C:15](=[O:17])[CH2:14][CH2:13][O:12][CH2:11][CH2:10][C:9]2[CH:18]=[CH:19][CH:20]=[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[CH:8]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 59224582N-(2,2-dimethoxyethyl)cycloheptanamineHCID 592904613-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid

Product 1

HCID 59290410N-Cycloheptyl-N-(2,2-dimethoxyethyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanamide

Reagents, catalysts & solvents 1

HCID 78922-MethylpentaneSolvent

Procedure

The subtitled compound (1.2 g) was prepared from 3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid [Example 2a, Step i)] and N-(2,2-dimethoxyethyl)cycloheptanamine [Preparation 6], using a similar method to that described in Preparation 3 Step iii) and the elution gradient used was 50-80% ethyl acetate in isohexane. 1H NMR (400 MHz, DMSO-d6) δ 8.10 and 8.09 (2×s, 1H), 7.82 (s, 1H), 7.44-7.40 (m, 1H), 7.37 (d, J=7.7 Hz, 1H), 7.26-7.21 (m, 1H), 7.06-7.02 (m, 1H), 4.51 and 4.39 (2×t, J=5.0 Hz, 1H), 3.85 (s, 3H), 3.86-3.66 (m, 1H), 3.68-3.56 (m, 4H), 3.31 (s, 3H), 3.30 and 3.16 (2×d, J=5.0 Hz, 2H), 3.25 (s, 3H), 2.81-2.76 (m, 2H), 2.61-2.51 (m, 2H), 1.79-1.23 (m, 12H); a ˜1:1 mixture of rotamers is observed.

Workup

  1. customthat described in Preparation 3 Step iii) and the elution gradient
  2. additiona ˜1:1 mixture of rotamers

Sources & evidence

ORD record
ord-fd3f184b08a849d98c008e95d9a0c3ab
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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