Hydrochloric Acid → HCID 59231993, compound

HRID 1099275Notes

Reaction equation

HRID 1099275 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[N:29]=4)=[O:26])=[CH:20][CH:19]=3)[CH:9]=[C:10]([C:11]([O:13]CCCC)=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1.[OH-].[Na+].Cl>C1COCC1.CO>[NH2:1][C:2]1[C:7]2=[C:8]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[N:29]=4)=[O:26])=[CH:20][CH:19]=3)[CH:9]=[C:10]([C:11]([OH:13])=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59232106HCID 59232106, compound

Product 1

HCID 59231993HCID 59231993, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of butyl 4-amino-5-{4-[({[6-(trifluoromethyl)pyridin-2-yl]amino}carbonyl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-7-carboxylate (96.0 mg, 0.19 mmol) and 1 N aqueous sodium hydroxide solution (0.94 mL, 0.94 mmol) in THF (4 mL) and MeOH (5 mL) was stirred at rt for 4 h and acidified to pH 3 using 2N hydrochloric acid. The organic solvents were evaporated under reduced pressure and the residue was suspended in water (5 mL). The solid was filtered, washed with water and air-dried to give 63.0 mg (74%) of the title compound. 1H-NMR (DMSO-d6) δ 12.76 (s, 1 H), 9.87 (s, 1 H), 9.71 (s, 1 H), 8.08 (s, 1 H), 8.04-7.97 (m, 2 H), 7.57 (d, J=8.6 Hz, 2 H), 7.50-7.49 (m, 1 H), 7.43 (d, J=8.5 Hz, 2 H), 7.20 (s, 1 H); MS [M+H]+=458.0; LCMS RT=2.90 min.

Workup

  1. customThe organic solvents were evaporated under reduced pressure
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-bcf95d68af344dc184474ef8ee767933
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

Loading…