Methanesulfonyl chloride → HCID 22053586, compound

HRID 1829671Notes

Reaction equation

[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][NH:11][C:10]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[C:9]=2[C:8]1=[O:30].C(OC([N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)=O)(C)(C)C.[CH3:53][S:54](Cl)(=[O:56])=[O:55]>>[F:38][C:2]([F:39])([F:1])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:33]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][NH:11][C:10]2[N:15]=[C:16]([N:50]3[CH2:51][CH2:52][N:47]([S:54]([CH3:53])(=[O:56])=[O:55])[CH2:48][CH2:49]3)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[C:9]=2[C:8]1=[O:30]

Participants

Reactant 3

HCID 31297Methanesulfonyl chloride

HCID 143452tert-Butyl piperazine-1-carboxylate

HCID 220535916-[3,5-Bis(trifluoromethyl)benzyl]-5,6,7,8,9,10-hexahydro-4-(2-methylphenyl)-2-(methylsulfonyl)-5-oxopyrimido[4,5-b][1,5]diazocine

Product 1

HCID 22053586HCID 22053586, compoundYield 75%

Procedure

In a similar manner to Example 24, 6-[3,5-bis(trifluoromethyl)benzyl]-5,6,7,8,9,10-hexahydro-4-(2-methylphenyl)-2-(methylsulfonyl)-5-oxopyrimido[4,5-b][1,5]diazocine (Compound of Reference Example 19; 85.9 mg), 1-(t-butoxycarbonyl)piperazine (33.5 mg) and methylsulfonylchloride (0.04 mL) were reacted to obtain 6-[3,5-bis(trifluoromethyl)benzyl]-5,6,7,8,9,10-hexahydro-4-(2-methylphenyl)-2-[4-(methylsulfonyl)piperazine-1-yl]-5-oxopyrimido[4,5-b][1,5]diazocine (74.1 mg, 75%).

Sources & evidence

ORD record: ord-1e3ab22fedd64f6ab1ea5dabaff6cfae
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064119B2

Reaction notes

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