Dimethylamine → HCID 21135734, compound

HRID 1358055Notes

Reaction equation

HRID 1358055 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=3)[CH:9]2[CH2:19][C:20]2[CH:28]=[C:27]3[C:23]([CH:24]=[C:25]([C:29]([OH:31])=O)[NH:26]3)=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[CH3:32][NH:33][CH3:34].O1CCCC1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=3)[CH:9]2[CH2:19][C:20]2[CH:28]=[C:27]3[C:23]([CH:24]=[C:25]([C:29]([N:33]([CH3:34])[CH3:32])=[O:31])[NH:26]3)=[CH:22][CH:21]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 18186403HCID 18186403, compound

Product 1

HCID 21135734HCID 21135734, compoundYield 48%

Procedure

The title compound was prepared as described in Example 34.B using 6-{[2-(4-fluorophenyl)-6-hydroxy-1,2,3,4-tetrahydroisoquinolyl]methyl}indole-2-carboxylic acid (0.25 g, 0.6 mmol) and 2.0 M solution of dimethylamine in tetrahydrofuran (1.0 mL, 2.0 mmol) to provide the title compound (0.127 g, 48% yield): 1H NMR (CDCl3) 9.05 (br, 1H), 7.52 (d, 1H), 7.26-6.76 (m, 7H), 6.61 (d, 1H), 6.57 (d, 1H), 6.50 (dd, 1H), 4.80 (t, 1H), 3.58 (m, 1H), 3.47 (m and s, 4H), 3.27 (dd, 1H), 3.20 (s, 3H), 3.03 (dd, 1H), 2.89 (m, 1H), 2.67 (dt, 1H); ES-MS m/z 444 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-700e44a0949e41eb9364437dd8f785d7
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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