Sodium Hydroxide → HCID 178508831, compound

HRID 2197532Notes

Reaction equation

HRID 2197532 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]4[NH:27][C:26]5[C:28]([F:33])=[CH:29][C:30]([F:32])=[CH:31][C:25]=5[N:24]=4)=[CH:18][CH:17]=3)[C:9]([C:11]([O:13]CC)=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[OH-].[Na+]>C1COCC1.CO>[NH2:1][C:2]1[C:7]2=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]4[NH:27][C:26]5[C:28]([F:33])=[CH:29][C:30]([F:32])=[CH:31][C:25]=5[N:24]=4)=[CH:18][CH:17]=3)[C:9]([C:11]([OH:13])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178469452HCID 178469452, compound

Product 1

HCID 178508831HCID 178508831, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (5.85 g, 13.0 mmol) in THF (300 mL) and methanol (100 mL) was added 1N aqueous sodium hydroxide solution (130 mL, 130 mmol). The reaction was stirred at rt overnight and then the solution was concentrated under reduced pressure. The residue was diluted in water (500 mL) and then the mixture was adjusted to pH 3 using concentrated hydrochloric acid. The resulting precipitate was collected by filtration and dried to yield the desired product (5.60 g, 100%) containing some trace impurities. 1H-NMR (300 MHz, DMSO-d6) δ 10.17 (s, 1H), 8.17-8.38 (br s, 1H) 8.14 (s, 1H), 7.97 (s, 1 H), 7.77 (d, J=8.0 Hz, 2H), 7.38 (d, J=8.0 Hz, 2H), 7.05 (d, J=8.1 Hz, 1H), 6.93 (dd, J=10.2, 10.2 Hz, 1H) 5.22-5.44 (br s, 1H); ES-MS m/z 422.1 (MH)+; HPLC RT (Method B) 2.13 min.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. additionThe residue was diluted in water (500 mL)
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-e3b052cf6fb445848ed9aaeac1f9471a
Source dataset
uspto-grants-2012_12
Patent number
US08338594B2

Reaction notes

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