Diisopropylethylamine → (rac)-Cyclopropanesulfonic acid [4-(3-fluoro-4-trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-yl]-amide

HRID 714099Notes

Reaction equation

HRID 714099 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[C:20]3[CH2:19][CH2:18][CH:17]([NH2:21])[C:16]=3[CH:15]=[N:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C(N(CC)C(C)C)(C)C.[CH:31]1([S:34](Cl)(=[O:36])=[O:35])[CH2:33][CH2:32]1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[C:20]3[CH2:19][CH2:18][CH:17]([NH:21][S:34]([CH:31]4[CH2:33][CH2:32]4)(=[O:36])=[O:35])[C:16]=3[CH:15]=[N:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:9])([F:11])[F:10]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 71811529(rac)-4-(3-Fluoro-4-trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-ylamine

Product 1

HCID 71811527(rac)-Cyclopropanesulfonic acid [4-(3-fluoro-4-trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-yl]-amideYield 3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (rac)-4-(3-fluoro-4-trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-ylamine (example 89) (40 mg, 0.14 mmol) and N,N-diisopropylethylamine (0.071 mL, 0.41 mmol) in DMF (0.5 mL) was treated with cyclopropanesulfonyl chloride (0.021 mL, 0.20 mmol) and the reaction mixture stirred at room temperature overnight. Purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 1.5 mg (3%) of the title compound as a light brown oil. MS: 401.4 (M+H)+.

Workup

  1. customPurification by preparative HPLC on reversed phase
  2. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-02d2e20f05f242859cad17293433d406
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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