Hydrochloric Acid → HCID 58563957, compound

HRID 336208Notes

Reaction equation

HRID 336208 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([CH:13]2[O:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.Br[C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=1.C(N(CC)CC)C>C(O)(C)(C)C>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([CH:13]2[O:18][CH2:17][CH2:16][N:15]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=3)[CH2:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 58563909HCID 58563909, compound

Product 1

HCID 58563957HCID 58563957, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
175 °C

Procedure

A microwave vial is charged with morpholine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide; hydrochloride (75 mg; 0.259 mmol), 2-bromo-5-trifluoromethylpyridine (58.8 mg; 0.26 mmol), triethylamine (0.072 mL; 0.52 mmol) and t-butanol (0.5 mL). The vial is heated in microwave at 175° C. for 1 hour then left standing at room temperature for 18 hours. After this time, the reaction mixture is concentrated in vacuo. Purification by flash chromatography using methanol/methylene chloride provides the title compound, m/z 399 [M+H+].

Workup

  1. waitthen left
  2. concentrationAfter this time, the reaction mixture is concentrated in vacuo
  3. customPurification by flash chromatography

Sources & evidence

ORD record
ord-345e5bf79e0d4266a7aa98f40b52a97e
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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