Methanesulfonyl chloride → HCID 86620633, compound

HRID 1436890Notes

Reaction equation

HRID 1436890 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[F:18])[CH2:5][N:6]1[CH2:11][CH2:10][C:9]([CH2:12][OH:13])=[CH:8][C:7]1=[O:14].CCN(C(C)C)C(C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[F:18])[CH2:5][N:6]1[CH2:11][CH2:10][C:9]([CH2:12][O:13][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:8][C:7]1=[O:14]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69060577HCID 69060577, compound

Product 1

HCID 86620633HCID 86620633, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(3-chloro-4-fluorobenzyl)-4-hydroxymethyl-5,6-dihydropyridin-2(1H)-one (3.1 g, 11 mmol) from the previous step and DIEA (2.8 mL, 16 mmol) in CH2Cl2 (50 mL) was cooled to 0° C. with stirring. Methanesulfonyl chloride (1.4 g, 12 mmol) was added and the mixture was stirred at 0° C. for 30 min and then at ambient temperature for 1 hour. The reaction mixture was diluted with CH2Cl2 (75 mL) and extracted with water (2×30 mL). The CH2Cl2 layer was dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give the title compound as a gum. 1H NMR (400 MHz, CDCl3) δ 7.31 (dd, J=6.9, 2.9 Hz, 1H), 7.1-7.2 (m, 2H), 4.64 (d, J=15 Hz, 1H), 4.44 (d, J=15 Hz, 1H), 4.13 (ABX, J=6, 15 Hz, 2H), 3.28 (m, 2H), 3.04 (s, 3H), 2.64 (m, 1H), 2.34 (m, 1H), 2.23 (dd, J=6, 16 Hz, 1H), 2.02 (m, 1H), 1.61 (m, 1H); HPLC RT=2.99 min (Method A); ES MS M+1=350.

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 min
  2. extractionextracted with water (2×30 mL)
  3. dry with materialThe CH2Cl2 layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4b24fc8852184249ba178402676020d9
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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