Methanesulfonyl chloride → HCID 178505326, compound

HRID 2200768Notes

Reaction equation

HRID 2200768 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:16][S:17]([O:15][C@H:12]1[CH2:11][CH2:10][C@H:9]([NH:8][C:5]2[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:14][CH2:13]1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 178521599HCID 178521599, compound

Product 1

HCID 178505326HCID 178505326, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As shown in step 6-ii of Scheme 6, to compound 1013 (1.2 g, 4.41 mmol) in DCM (20 mL) was added TEA (1.134 g, 1.84 mL, 13.2 mmol) and MsCl (505 mg, 341 μL, 4.41 mmol). The reaction mixture was stirred for 1 hour, concentrated under reduced pressure, and purified by medium pressure silica gel chromatography (0 to 80% EtOAc/hexanes gradient) to provide trans-4-((5-bromopyrimidin-2-yl)amino)cyclohexyl methanesulfonate (compound 1014): 1H-NMR (300 MHz, CDCl3) δ 8.29 (s, 2H), 5.03 (d, J=7.8 Hz, 1H), 4.70 (tt, J=10.6, 3.9 Hz, 1H), 3.80 (dtt, J=11.2, 7.6, 3.7 Hz, 1H), 3.04 (s, 3H), 2.30-2.12 (m, 4H), 1.93-1.69 (m, 2H), 1.51-1.33 (m, 2H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by medium pressure silica gel chromatography (0 to 80% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-8f0078a2f89d4b839f602534cc2cce81
Source dataset
uspto-grants-2016_06
Patent number
US09359380B2

Reaction notes

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