(R)-N-(2,2-dimethoxyethyl)pentan-2-amine → (R)-N-(2,2-Dimethoxyethyl)-3-(3-(1-isopropyl-1H-pyrazol-4-yl)phenethoxy)-N-(pentan-2-yl)propanamide

HRID 909936Notes

Reaction equation

HRID 909936 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]([CH2:30][CH2:31][CH3:32])[CH3:29]>>[CH3:23][O:24][CH:25]([O:33][CH3:34])[CH2:26][N:27]([C@@H:28]([CH2:30][CH2:31][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]=1

Participants

3

Reactant 2

HCID 59290396(R)-N-(2,2-dimethoxyethyl)pentan-2-amineHCID 59290435HCID 59290435, compound

Product 1

HCID 59290426(R)-N-(2,2-Dimethoxyethyl)-3-(3-(1-isopropyl-1H-pyrazol-4-yl)phenethoxy)-N-(pentan-2-yl)propanamide

Procedure

The subtitled compound (100 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)pentan-2-amine [Preparation 10] 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), 7.79 (s, 1H), 7.42-7.34 (m, 2H), 7.23 (t, J=7.7 Hz, 1H), 7.05 (d, J=7.7 Hz, 1H), 4.56 and 4.40 (2×t, J=5.3 Hz, 1H), 4.53 (septet, J=6.7 Hz, 1H), 4.26-4.16 and 3.96-3.86 (2×m, 1H), 3.75-3.64 (m, 4H), 3.34 (s, 3H), 3.32 (s, 3H), 3.25-3.10 (m, 2H), 2.84 (t, J=6.5 Hz, 2H), 2.72-2.50 (m, 2H), 1.60-1.14 (m, 4H), 1.51 (d, J=6.9 Hz, 6H), 1.10 and 1.09 (2×d, J=6.7 Hz, 3H), 0.86 (t, J=7.3 Hz, 3H); a ˜1:1 mixture of rotamers is observed.

Workup

  1. additiona ˜1:1 mixture of rotamers

Sources & evidence

ORD record
ord-edb6e71a392e49dea69a47e420c2dde8
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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