Ethanolamine → HCID 18186404, compound

HRID 1358045Notes

Reaction equation

HRID 1358045 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]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]=3)[CH:9]2[CH2:26][C:27]2[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]/[C:35]([OH:37])=O)=[CH:29][CH:28]=2)=[CH:4][CH:3]=1.[CH2:38]([CH2:40][NH2:41])[OH:39]>>[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]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]=3)[CH:9]2[CH2:26][C:27]2[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]/[C:35]([NH:41][CH2:40][CH2:38][OH:39])=[O:37])=[CH:29][CH:28]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 18186380HCID 18186380, compound

Product 1

HCID 18186404HCID 18186404, compoundYield 60%

Procedure

The title compound was prepared as described in Example 34.B using (2E)-3-(4-{[2-(4-fluorophenyl)-6-(phenylmethoxy)( 1,2,3,4-tetrahydroisoquinolyl)]methyl}phenyl)prop-2-enoic acid (0.494 g, 1.0 mmol) and ethanolamine (0.122 g, 2.0 mmol) to provide the title compound (0.322 g, 60% yield): 1H NMR (CDCl3) 8.02 (br, 1H), 7.61 (d, 1H), 7.32-7.41 (m, 7H), 7.00 (d, 2H), 6.91 (m, 2H), 6.69-6.77 (m, 5H), 6.37 (d, 1H), 6.12 (t, 1H), 5.03 (s, 2H), 4.75 (t, 1H), 3.80 (t, 2H), 3.57 (t, 2H), 3.45-3.56 (m 2H), 3.15 (dd, 1H), 2.89 (m, 2H), 2.66 (dt, 1H); ES-MS m/z 537 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-ea34c752f6dc4158ad46cd5d2e2bc9ce
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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