Isopropanol → HCID 89906961, compound

HRID 924000Notes

Reaction equation

HRID 924000 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].Cl.[NH2:24][CH2:25][CH2:26][OH:27].CC(O)C.CCN(C(C)C)C(C)C>O>[Br:1][C:2]1[C:3]([NH:24][CH2:25][CH2:26][OH:27])=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 74819Ethanolamine HydrochlorideHCID 81531DiisopropylethylamineHCID 867025955-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 89906961HCID 89906961, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 12.2, 0.5 g, 1.264 mmol), 2-aminoethanol hydrochloride (0.123 g, 1.896 mmol), iPrOH (4 mL) and DIPEA (0.442 mL, 0.327 g, 2.53 mmol) were subjected to MW irradiation at 140° C. for 2 h. The vial was cooled to RT and the RM was poured into water (100 mL) and the resulting precipitate was collected by filtration. The obtained solid was washed with water (50 mL) and dried to afford the title compound without further purification. LC-MS (Condition 6) tR=1.14 min, m/z=419.8 [M+H]+.

Workup

  1. customwere subjected to MW irradiation at 140° C. for 2 h
  2. filtrationthe resulting precipitate was collected by filtration
  3. washThe obtained solid was washed with water (50 mL)
  4. customdried

Sources & evidence

ORD record
ord-92137534bb504ee7bfa715a73df54a02
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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