(7R)-7-({[t-Butyl(dimethyl)silyl]oxy}methyl)-7-methyl-5-(methylthio)-2,3,6,7-tetrahydro-1,4-thiazepine → (8R)-8-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-3-{1-[4-(2-methylpyrimidin-5-yl)phenyl]cyclopropyl}-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

HRID 1424137Notes

Reaction equation

HRID 1424137 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:17]([NH:19][NH2:20])=O)[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][N:3]=1.[Si:21]([O:28][CH2:29][C@:30]1([CH3:39])[S:36][CH2:35][CH2:34][N:33]=[C:32](SC)[CH2:31]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(O)(C)(C)C>[Si:21]([O:28][CH2:29][C@:30]1([CH3:39])[S:36][CH2:35][CH2:34][N:33]2[C:17]([C:14]3([C:11]4[CH:12]=[CH:13][C:8]([C:5]5[CH:6]=[N:7][C:2]([CH3:1])=[N:3][CH:4]=5)=[CH:9][CH:10]=4)[CH2:15][CH2:16]3)=[N:19][N:20]=[C:32]2[CH2:31]1)([C:24]([CH3:27])([CH3:25])[CH3:26])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 71466071(7R)-7-({[t-Butyl(dimethyl)silyl]oxy}methyl)-7-methyl-5-(methylthio)-2,3,6,7-tetrahydro-1,4-thiazepineHCID 867129811-[4-(2-Methylpyrimidin-5-yl)phenyl]cyclopropanecarbohydrazide

Product 1

HCID 86712982(8R)-8-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-3-{1-[4-(2-methylpyrimidin-5-yl)phenyl]cyclopropyl}-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepineYield 74%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of the compound (591 mg, 2.23 mmol) obtained in Example 88-1) and the compound (750 mg, 2.35 mmol) obtained in Example 4-1) in t-butanol (10 mL) was stirred for 7 h under reflux conditions. The obtained reaction mixture was cooled to room temperature and concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (methanol:ethyl acetate=10:90 to 100:0) to obtain the title compound (861 mg, 70%) as a light yellow solid.

Workup

  1. customThe obtained reaction mixture
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (methanol:ethyl acetate=10:90 to 100:0)

Sources & evidence

ORD record
ord-9c29d0a794504993b24cf5e04bd29528
Source dataset
uspto-grants-2015_01
Patent number
US08927536B2

Reaction notes

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