Hydrochloric Acid → HCID 53241391, compound

HRID 1027604Notes

Reaction equation

HRID 1027604 reaction equation
[NH2:1][CH2:2][CH:3]([OH:32])[CH2:4][NH:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:17][C:16]([C:22]3[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=3)([C:18]([F:21])([F:20])[F:19])[O:15][N:14]=2)=[CH:9][C:8]=1[CH3:30].N1C=CC=CC=1.[S:39](Cl)(Cl)=[O:40].Cl>ClCCl>[Cl:28][C:26]1[CH:27]=[C:22]([C:16]2([C:18]([F:20])([F:21])[F:19])[O:15][N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([C:6]([NH:5][CH2:4][CH:3]4[O:32][S:39](=[O:40])[NH:1][CH2:2]4)=[O:31])=[C:8]([CH3:30])[CH:9]=3)[CH2:17]2)[CH:23]=[C:24]([Cl:29])[CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 67260076HCID 67260076, compound

Product 1

HCID 53241391HCID 53241391, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-(3-amino-2-hydroxy-propyl)-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzamide (0.2 g) in dichloromethane (10 ml) was cooled to 0° C., treated with pyridine (0.32 ml) and thionyl chloride (0.06 ml), and stirred for 4 hours. The mixture was diluted with dichloromethane (50 ml), neutralized with 2N hydrochloric acid, and washed with water (50 ml). The organic layer was separated, dried over sodium sulfate and concentrated. Purification by chromatography on silica gel (eluent hexane/ethyl acetate 40:60) gave the title compound (20 mg). LCMS (Method G) 3.88 min, (M−H)− 534. 1HNMR (CDCl3, 400 MHz): 7.45-7.52 (m, 6H), 6.50 (m, 1H), 4.05 (d, 1H), 3.98 (m, 1H), 3.72 (d, 1H), 3.62 (m, 1H), 3.51 (m, 3H), 2.46 (s, 3H).

Workup

  1. washwashed with water (50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by chromatography on silica gel (eluent hexane/ethyl acetate 40:60)

Sources & evidence

ORD record
ord-5738d3ee074e4ee8af2355142ff3f855
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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