Methanesulfonyl chloride → HCID 86638748, compound

HRID 423624Notes

Reaction equation

HRID 423624 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH3:16][Mg]Br.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>CCN(CC)CC>[CH3:19][S:20]([O:15][CH:14]([CH:11]1[CH2:12][CH2:13][N:8]([C:5]2[N:6]=[CH:7][C:2]([F:1])=[CH:3][N:4]=2)[CH2:9][CH2:10]1)[CH3:16])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 866387471-(5-Fluoro-2-pyrimidinyl)-4-piperidinecarbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 86638748HCID 86638748, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

(±)-1-[1-(5-Fluoro-2-pyrimidinyl)-4-piperidinyl]ethyl methanesulfonate (0.24 g) was prepared as a colorless oil from 1-(5-fluoro-2-pyrimidinyl)-4-piperidinecarbaldehyde and methylmagnesium bromide (3M in Et2O) then methanesulfonyl chloride and Et3N in a manner similar to Example 139, Steps 1-2. The crude product was purified by chromatography on an ISCO silica gel column using 0 to 40% EtOAc/hexanes to give (±)-1-[1-(5-fluoro-2-pyrimidinyl)-4-piperidinyl]ethyl methanesulfonate as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 8.17 (s, 2H), 4.80-4.70 (m, 2H), 4.70-4.60 (m, 1H), 2.99 (s, 3H), 2.90-2.75 (m, 2H), 1.95-1.70 (m, 3H), 1.40 (d, 3H, J=6.3 Hz), 1.35-1.25 (m, 2H); LRMS (ESI), m/z 304 (M+H).

Workup

  1. customThe crude product was purified by chromatography on an ISCO silica gel column

Sources & evidence

ORD record
ord-37ad24de4c664e2d83af033e1d915bc1
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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