Methanol → HCID 72201876, compound

HRID 629074Notes

Reaction equation

HRID 629074 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:26]=[CH:25][C:10]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)=[O:12])=[CH:9][C:8]=1[C:27]1[CH:28]=[N:29][CH:30]=[N:31][CH:32]=1.CO>C(Cl)Cl>[OH:6][C:7]1[CH:26]=[CH:25][C:10]([C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:21]([F:22])([F:23])[F:24])=[CH:18][CH:19]=2)=[O:12])=[CH:9][C:8]=1[C:27]1[CH:32]=[N:31][CH:30]=[N:29][CH:28]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 72201590HCID 72201590, compound

Product 1

HCID 72201876HCID 72201876, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

BBr3 1 M in DCM (3.85 mL, 3.85 mmol) was added dropwise to a stirred solution of 4-methoxy-3-(pyrimidin-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide (100 mg, 0.257 mmol) in DCM (1.027 mL) at −70° C. and then stirred at RT for 2.5 days and under reflux for 2 days. The RM was treated with MeOH and the solvent was evaporated off under reduced pressure to give the crude product was purified by preparative HPLC (Condition 8, 50% for 0.2 min then 50% to 100% in 15 min) to yield the title compound as a white solid. UPLC-MS (Condition 1) tR=2.29 min, m/z=376.0 [M+H]+, m/z=374.0 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.13 (d, J=8.6 Hz, 1H) 7.36 (d, J=8.6 Hz, 2H) 7.87 (d, J=9.0 Hz, 2H) 7.93 (dd, J=8.6, 2.2 Hz, 1H) 8.09 (d, J=2.0 Hz, 1H) 9.09 (s, 2H) 9.17 (s, 1H) 10.24 (s, 1H) 10.82 (br. s, br. s, 1H).

Workup

  1. temperatureunder reflux for 2 days
  2. customthe solvent was evaporated off under reduced pressure
  3. customto give the crude product
  4. customwas purified by preparative HPLC (Condition 8, 50% for 0.2 min

Sources & evidence

ORD record
ord-1f608db0cbf04308a335e073bd962a01
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

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