Water → HCID 57713871, compound

HRID 1984320Notes

Reaction equation

HRID 1984320 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N:6]1([C:13]2[N:18]=[C:17]([CH:19]3[CH2:21][CH2:20]3)[N:16]=[C:15]([N:22]3[CH2:25][CH:24]([OH:26])[CH2:23]3)[C:14]=2[CH3:27])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(N(CC)CC)C.O>ClCCl>[N:6]1([C:13]2[N:18]=[C:17]([CH:19]3[CH2:20][CH2:21]3)[N:16]=[C:15]([N:22]3[CH2:23][CH:24]([O:26][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:25]3)[C:14]=2[CH3:27])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44430462HCID 44430462, compound

Product 1

HCID 57713871HCID 57713871, compoundYield 111%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of methanesulfonyl chloride (0.63 ml, 7.6 mmol) in dichloromethane (10 ml) is added dropwise to a solution of 1-(6-azepan-1-yl-2-cyclopropyl-5-methyl-pyrimidin-4-yl)-azetidin-3-ol 189 (1.90 g, 6.3 mmol) and triethylamine (1.74 ml, 13 mmol) in dichloromethane (90 ml) at 0° C. The mixture is stirred 1 hour at 0° C. and 1 hour at room temperature. Water (40 ml) is added and the mixture is extracted three times with dichloromethane. The combined organic layers are dried over magnesium sulfate and concentrated in vacuo to afford pure methanesulfonic acid 1-(6-azepan-1-yl-2-cyclopropyl-5-methyl-pyrimidin-4-yl)-azetidin-3-yl ester 190 (2.66 g, 100%).

Workup

  1. extractionthe mixture is extracted three times with dichloromethane
  2. dry with materialThe combined organic layers are dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a22bed520ba421ab7bd9816d2871b09
Source dataset
uspto-grants-2009_06
Patent number
US07544675B2

Reaction notes

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