Benzyloxyamine hydrochloride → HCID 18186377, compound

HRID 1358044Notes

Reaction equation

HRID 1358044 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](O)=[O:36])=[CH:29][CH:28]=2)=[CH:4][CH:3]=1.Cl.[CH2:39]([O:46][NH2:47])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C1C=CN=CC=1)C>[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]([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:28]=[CH:29][C:30](/[CH:33]=[CH:34]/[C:35]([NH:47][O:46][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:36])=[CH:31][CH:32]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 18186380HCID 18186380, compound

Product 1

HCID 18186377HCID 18186377, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

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 (0.365 g, 0.74 mmol), O-benzylhydroxylamine hydrochloride (0.16 g, 1.0 mmol), and 4-(N,N-dimethylamino)pyridine (0.121 g, 1.0 mmol) to provide the title compound (0.323 g, 73% yield): 1H NMR (CDCl3) 8.00 (br, 1H), 7.70 (d, 1H), 7.30-7.42 (m, 12H), 7.01 (d, 2H), 2.92 (m, 2H), 6.66-6.82 (m, 6H), 5.03 (s, 2H), 4.97 (s, 2H), 4.75 (t, 1H), 3.56 (m, 1H), 3.47 (m, 1H), 3.17 (dd, 1H), 2.88-3.00 (m, 2H), 2.66 (dt, 1H); ES-MS m/z 599 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-cce297178f844d8a9e4bdf61042f4aa6
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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