(R)-N-(2,2-dimethoxyethyl)-3-methylbutan-2-amine → (R)-N-(2,2-Dimethoxyethyl)-3-(3-(1-isopropyl-1H-pyrazol-4-yl)phenethoxy)-N-(3-methylbutan-2-yl)propanamide
Reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=2)[CH2:12][CH2:13][O:14][CH2:15][CH2:16][C:17]([OH:19])=O)[CH:6]=[N:5]1)([CH3:3])[CH3:2].[CH3:23][O:24][CH:25]([O:33][CH3:34])[CH2:26][NH:27][C@@H:28]([CH:30]([CH3:32])[CH3:31])[CH3:29]>>[CH3:23][O:24][CH:25]([O:33][CH3:34])[CH2:26][N:27]([C@@H:28]([CH:30]([CH3:31])[CH3:32])[CH3:29])[C:17](=[O:19])[CH2:16][CH2:15][O:14][CH2:13][CH2:12][C:11]1[CH:20]=[CH:21][CH:22]=[C:9]([C:7]2[CH:6]=[N:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH:8]=2)[CH:10]=1Participants
Procedure
The subtitled compound (105 mg) was prepared from 3-(3-(1-isopropyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid [Example 20, Step iii)] and (R)—N-(2,2-dimethoxyethyl)-3-methylbutan-2-amine, prepared as in Preparation 4 using a similar method to that described in Example 18, Step iii). MS [M+H-MeOH]+=428 (MultiMode+) 1H NMR (400 MHz, CD3OD) δ 8.01 and 8.00 (2×s, 1H), 7.78 (s, 1H), 7.42-7.33 (m, 2H), 7.23 and 7.22 (2×t, J=7.8 Hz, 1H), 7.05 (d, J=7.6 Hz, 1H), 4.59 and 4.43 (2×t, J=5.1 Hz, 1H), 4.53 (septet, J=7.0 Hz, 1H), 3.76-3.63 (m, 5H), 3.37-3.27 (m, 8H), 2.85 and 2.84 (2×t, J=6.8 Hz, 2H), 2.75-2.49 (m, 2H), 1.97-1.85 and 1.78-1.66 (2×m, 1H), 1.51 (d, J=6.9 Hz, 6H), 1.15 and 1.14 (2×d, J=6.9 Hz, 3H), 0.90 and 0.87 (2×d, J=6.8 Hz, 3H), 0.79 and 0.74 (2×d, J=6.3 Hz, 3H); a ˜1:1 mixture of rotamers is observed.
Workup
- additiona ˜1:1 mixture of rotamers
Sources & evidence
- ORD record
- ord-023e90dd6b1b45f7a3845272fd4f0986
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017602B2
Reaction notes
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