Acetic Anhydride → 9-(4-acetylhomopiperazine-1-yl)-5-[3,5-bis(trifluoromethyl)benzyl]-6-oxo-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine

HRID 1795012Notes

Reaction equation

HRID 1795012 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][O:11][C:10]2[N:15]=[C:16](Cl)[CH:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]=2[C:8]1=[O:26].C([O:40][C:41]([N:43]1[CH2:49][CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)=O)(C)(C)C.[C:50](OC(=O)C)(=O)C>>[C:41]([N:43]1[CH2:49][CH2:48][CH2:47][N:46]([C:16]2[CH:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]3[C:8](=[O:26])[N:7]([CH2:6][C:5]4[CH:4]=[C:3]([C:2]([F:35])([F:34])[F:1])[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=4)[CH2:14][CH2:13][CH2:12][O:11][C:10]=3[N:15]=2)[CH2:45][CH2:44]1)(=[O:40])[CH3:50]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 221793335-[3,5-bis(trifluoromethyl)benzyl]-9-chloro-6-oxo-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine

Product 1

HCID 221844329-(4-acetylhomopiperazine-1-yl)-5-[3,5-bis(trifluoromethyl)benzyl]-6-oxo-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocineYield 51%

Procedure

In a similar manner to Example 6, 5-[3,5-bis(trifluoromethyl)benzyl]-9-chloro-6-oxo-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (compound of Reference Example 15; 52.0 mg) was reacted with 1-(t-butoxycarbonyl)homopiperazine (50.6 mg) and acetic anhydride (50 μL) to obtain 9-(4-acetylhomopiperazine-1-yl)-5-[3,5-bis(trifluoromethyl)benzyl]-6-oxo-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (31.7 mg, 51%).

Sources & evidence

ORD record
ord-a62939f4f82841069f476cb0bdb08a18
Source dataset
uspto-grants-2006_04
Patent number
US07026309B2

Reaction notes

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