Hydrochloric Acid → HCID 58020204, compound

HRID 1632033Notes

Reaction equation

HRID 1632033 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=3)[C:9]=2[F:24])[CH:5]=[CH:6][CH:7]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].Cl>N1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([NH:23][S:26]([CH3:25])(=[O:28])=[O:27])=[N:21][CH:22]=3)[C:9]=2[F:24])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 57703709HCID 57703709, compound

Product 1

HCID 58020204HCID 58020204, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 5-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridin-2-ylamine (P-252) synthesized above (70 mg, 0.18 mmol) in pyridine (2 ml) was added methanesulfonyl chloride (23 mg, 0.20 mmol) at 0 C under nitrogen, and stirred at room temperature for 20 h. The reaction mixture was diluted with water, neutralized with 6N HCl, extracted with ethyl acetate, washed with water and brine, and dried over Na2SO4. After it was concentrated in vacuo, the residue was purified by a chromatography on silica gel to yield N-[5-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridin-2-yl]-methanesulfonamide (P-258) (25 mg, 32%). 1H NMR (400 MHz, CDCl3) 8.15 (s, 1H), 7.58 (dd, J=8.8, 2.1 Hz, 1H), 7.38 (s, 1H), 7.34 (t, J=6.6 Hz, 3H), 7.24-7.31 (m, 2H), 7.11 (t, J=8.5 Hz, 1H), 6.73 (d, J=8.5 Hz, 1H), 3.89 (s, 2H), 3.77 (s, 3H), 3.09 (s, 3H) ppm.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter it was concentrated in vacuo
  5. customthe residue was purified by a chromatography on silica gel

Sources & evidence

ORD record
ord-8513f73eded3437e81ac2297a1f681c6
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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