Methanesulfonyl chloride → HCID 22184424, compound

HRID 1795015Notes

Reaction equation

HRID 1795015 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=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][C:22]([F:25])=[CH:21][CH:20]=3)[C:9]=2[C:8]1=[O:27].C(OC([N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)=O)(C)(C)C.[CH3:50][S:51](Cl)(=[O:53])=[O:52]>>[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][O:11][C:10]2[N:15]=[C:16]([N:47]3[CH2:48][CH2:49][N:44]([S:51]([CH3:50])(=[O:53])=[O:52])[CH2:45][CH2:46]3)[CH:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:9]=2[C:8]1=[O:27]

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 22179324HCID 22179324, compound

Product 1

HCID 22184424HCID 22184424, compoundYield 24%

Procedure

In a similar manner to Example 6, 5-[3,5-bis(trifluoromethyl)benzyl]-9-chloro-7-(4-fluorophenyl)-6-oxo-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (compound of Reference Example 16; 80.0 mg) was reacted with 1-(t-butoxycarbonyl)piperazine (70.0 mg) and methylsulfonyl chloride (60 μL) to obtain 5-[3,5-bis(trifluoromethyl)benzyl]-7-(4-fluorophenyl)-9-[4-(methylsulfonyl)piperazine-1-yl]-6-oxo-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (23.5 mg, 24%).

Sources & evidence

ORD record
ord-f88d8835981f428693af85953004d490
Source dataset
uspto-grants-2006_04
Patent number
US07026309B2

Reaction notes

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