Acetic Acid → HCID 22396257, compound

HRID 1070525Notes

Reaction equation

HRID 1070525 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5][N:6]1[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1.[F:17][C:18]([F:33])([F:32])[O:19][C:20]1[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([NH:28][NH2:29])=[O:27])=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH:29][NH:28][C:26](=[O:27])[CH2:25][O:24][C:23]2[CH:22]=[CH:21][C:20]([O:19][C:18]([F:17])([F:33])[F:32])=[CH:31][CH:30]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 27773052-[4-(trifluoromethoxy)phenoxy]acetohydrazideHCID 5049666Sodium triacetoxyborohydrideHCID 108487763,4-dichlorobenzyl-4-piperidone

Product 1

HCID 22396257HCID 22396257, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 3,4-dichlorobenzyl-4-piperidone (J. Med. Chem, 1999, 42, 3629; 100 mg), 2-[4(trifluoromethoxy)phenoxy]acetohydrazide (100 mg), sodium triacetoxyborohydride (100 mg), and 0.02 ml acetic acid, stirred together for 2 hours in dichloromethane by the method of Example 369 step ii. MS [M+H]+ (ES+) 492 1H NMR: (CDCl3) δ 1.4-1.6 (3H, m) 1.7 (2H, m), 2.0 (2H, m) 2.7-2.9 (2H, m), 3.4 (2H, m), 4.4 (3H, m), 5.3 (1H, s) 6.9 (2H, m), 7.2-7.5 (4H, m), 7.8 (1H, d).

Sources & evidence

ORD record
ord-64ce8947ff4a48b0843708e1725defda
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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