Methanesulfonyl chloride → HCID 86615300, compound

HRID 2264508Notes

Reaction equation

HRID 2264508 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[CH:19][C:18]([OH:21])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[N:20]=[CH:19][C:18]([O:21][S:32]([CH3:31])(=[O:34])=[O:33])=[CH:17][N:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68779108HCID 68779108, compound

Product 1

HCID 86615300HCID 86615300, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(5-hydroxy-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.74 g, 2.5 mmol, 1.0 equiv) in dichloromethane (20 mL) were added N-ethyl diisopropylamine (1.09 mL, 0.82 g, 6.3 mmol, 2.5 equiv), followed by methanesulfonyl chloride (0.24 mL, 0.35 g, 3.0 mmol, 1.2 equiv). After stirring for 4 h, the reaction mixture was poured into ice water and extracted twice with dichloromethane. The combined organic layers were washed with water, then dried over MgSO4, filtered and concentrated by evaporation under reduced pressure. The crude product was purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol to give 0.87 g (93%) of the title compound as colorless foam. MS (ISP): 373.1 [M+H]+.

Workup

  1. extractionextracted twice with dichloromethane
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe crude product was purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol

Sources & evidence

ORD record
ord-aea8d9d930a74a93b86f89c2fd9f31da
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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