Ethanesulfonylchloride, 2-chloro- → Tak-137

HRID 1748036Notes

Reaction equation

HRID 1748036 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[O:10]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24]([NH2:29])=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[O:10]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24]3=[N:29][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:25]3[CH:26]=[CH:27][CH:28]=2)=[CH:19][CH:18]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 655512093-(4-Phenoxyphenyl)pyridin-2-amine

Product 1

HCID 56649286Tak-137

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (60%, 20.4 g) in THF (dry) (250 mL) was added 2-chloroethanesulfonyl chloride (32.2 mL) at 0° C. and the mixture was stirred for 5 min at the same temperature. A solution of 3-(4-phenoxyphenyl)pyridin-2-amine (29.09 g) in THF (dry) (150 ml) was dropwised at 0° C. and the mixture was stirred at room temperature under N2 for 2 days. The mixture was quenched with THF/water (v/v=5/1) at 0° C. under N2 carefully. Water (500 mL) and EtOAc (400 mL) were added to form precipitates (stirred for 30 min) which were washed with water and EtOAc, collected and crystallized from DMSO/EtOH (500 mL/1000 ml, at 90° C.) to give the title compound (36.0 g) as colorless crystals.

Workup

  1. customwas dropwised at 0° C.
  2. stirringthe mixture was stirred at room temperature under N2 for 2 days
  3. customThe mixture was quenched with THF/water (v/v=5/1) at 0° C. under N2 carefully
  4. additionWater (500 mL) and EtOAc (400 mL) were added to form
  5. customprecipitates
  6. stirring(stirred for 30 min) which
  7. washwere washed with water and EtOAc
  8. customcollected
  9. customcrystallized from DMSO/EtOH (500 mL/1000 ml, at 90° C.)

Sources & evidence

ORD record
ord-954af822182b4fc4b4e71f07471448a3
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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