4-tert-Butylbenzylamine → HCID 22032681, compound

HRID 586050Notes

Reaction equation

HRID 586050 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:13]([O:17][C:18](=[O:34])[CH2:19][CH:20]([C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][N:28]=[CH:29]2)[C:21](O)=[O:22])([CH3:16])([CH3:15])[CH3:14].C1C2C(=C(CC(O)=O)C=CC=2)C=CN=1>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:21](=[O:22])[CH:20]([C:24]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:25]=2[CH:26]=[CH:27][N:28]=[CH:29]3)[CH2:19][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:34])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 27356554-tert-ButylbenzylamineHCID 120187082-(Isoquinolin-5-YL)acetic acidHCID 223375714-tert-butoxy-2-(5-isoquinolinyl)-4-oxobutanoic Acid

Product 1

HCID 22032681HCID 22032681, compound

Procedure

The title compound was prepared using the procedure described in Example 222B using 4-(tert-butyl)benzylamine and 4-tert-butoxy-2-(5-isoquinolinyl)-4-oxobutanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 447 (M+H)+; 1H NMR (DMSO, 300 MHz) δ 1.23 (s, 9H), 1.25 (s, 9H), 2.71 (dd, 1H), 3.02 (dd, 1H), 4.22 (m, 2H), 4.71 (m, 1H), 6.57 (s, 1H), 7.08 (d, J 8.5, 2H), 7.24 (d, J 8.5, 2H), 7.67 (m, 1H), 7.78 (m, 1H), 8.03 (d, J 7.8, 1H), 8.13 (d, J 7.1, 1H), 8.55 (d, J 6.8, 1H), 8.63 (m, 1H), 9.31 (s, 1H); Anal. Calcd for C28H34N2O3+1 CH3CN+0.8H2O: C, 71.77; H, 7.75; N, 8.37. Found: C, 71.64; H, 7.38; N, 8.16.

Sources & evidence

ORD record
ord-c0d71aa4be7d4b10b97d6ee97d5acea0
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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