Methanol → 1-{3-[(4-aminopyrrolo[2,1-f][1,2,4]triazin-5-yl)carbonyl]phenyl}-3-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)urea

HRID 2108358Notes

Reaction equation

HRID 2108358 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([NH:23][C:24]4[N:28]([CH3:29])[N:27]=[C:26]([CH:30]5[CH2:32][CH2:31]5)[CH:25]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:9]=[C:10](Br)[N:6]2[N:5]=[CH:4][N:3]=1.CO>CCOC(C)=O.[Pd]>[NH2:1][C:2]1[C:7]2=[C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([NH:23][C:24]4[N:28]([CH3:29])[N:27]=[C:26]([CH:30]5[CH2:32][CH2:31]5)[CH:25]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:9]=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 167397611-{3-[(4-amino-7-bromopyrrolo[2,1-f][1,2,4]triazin-5-yl)carbonyl]phenyl}-3-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)urea

Product 1

HCID 576294761-{3-[(4-aminopyrrolo[2,1-f][1,2,4]triazin-5-yl)carbonyl]phenyl}-3-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)urea

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The above crude 99A was dissolved in EtOAc (20 mL) and MeOH (20 mL) and treated with 10% Pd/C. The reaction mixture was stirred under a hydrogen atmosphere for 4.5 hours and then filtered to remove the catalyst. The filtrate was concentrated and the resulting solid was collected by filtration, rinsed with EtOAc and dried to give the desired product (23 mg). Compound 99B had an analytical HPLC retention time=2.433 min. (Chromolith SpeedROD column 4.6×50 mm, 10%-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 ml/min, monitoring at 220 nm) and a LC/MS M++1=417+.

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated
  4. filtrationthe resulting solid was collected by filtration
  5. washrinsed with EtOAc
  6. customdried

Sources & evidence

ORD record
ord-36660a6ed9bf474389d37f85a23ad5fc
Source dataset
uspto-grants-2009_04
Patent number
US07514435B2

Reaction notes

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