Methanesulfonyl chloride → HCID 22053557, compound

HRID 1829673Notes

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([NH:47][CH:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1)=O)(C)(C)C.[CH3:54][S:55](Cl)(=[O:57])=[O:56]>>[F:35][C:34]([F:37])([F:36])[C:32]1[CH:31]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:38])[F:39])[CH:33]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][NH:11][C:10]2[N:15]=[C:16]([N:51]3[CH2:52][CH2:53][CH:48]([NH:47][S:55]([CH3:54])(=[O:57])=[O:56])[CH2:49][CH2:50]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 7238334-(N-Boc-amino)piperidine

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 22053557HCID 22053557, compoundYield 45%

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), 4-(t-butoxycarbonylamino)piperidine (36.1 mg) and methanesulfonylchloride (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-(methylsulfonylamino)piperidine-1-yl]-5-oxopyrimido[4,5-b][1,5]diazocine (45.2 mg, 45%).

Sources & evidence

ORD record: ord-17c4ca693be247289d63a3e913698a88
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064119B2

Reaction notes

Loading…