Tetrahydrofuran → 6-[4-(5-Cyclopropyl-2H-pyrazol-3-ylamino)-6-iodo-quinazolin-2-ylamino]-1,2-dihydro-indazol-3-one

HRID 855654Notes

Reaction equation

HRID 855654 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][C:13]2[NH:14][N:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([I:21])[CH:8]=2)[N:3]=1.C(OC([N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([NH2:38])[CH:36]=2)[C:31](=[O:39])[NH:30]1)=O)(C)(C)C.C1COCC1.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[CH:18]1([C:16]2[CH:17]=[C:13]([NH:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[C:7]([I:21])[CH:8]=4)[N:3]=[C:2]([NH:38][C:35]4[CH:36]=[C:37]5[C:32]([C:31](=[O:39])[NH:30][NH:29]5)=[CH:33][CH:34]=4)[N:11]=3)[NH:14][N:15]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 574980196-Amino-3-oxo-2,3-dihydro-indazole-1-carboxylic acid tert-butyl esterHCID 178478383HCID 178478383, compound

Product 1

HCID 1785188486-[4-(5-Cyclopropyl-2H-pyrazol-3-ylamino)-6-iodo-quinazolin-2-ylamino]-1,2-dihydro-indazol-3-oneYield 95%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To (2-Chloro-6-iodo-quinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine (208 mg, 0.606 mmol) in NMP (1 mL) was added 6-Amino-3-oxo-2,3-dihydro-indazole-1-carboxylic acid tert-butyl ester (252 mg, 1.01 mmol) and THF (3 mL) and the solution was heated to 100 C in a sealed tube. After 4 h, the solution was poured into sat. NaHCO3, and extracted with ethyl acetate, dried (Na2SO4) and concentrated in vacuum to give the title compound as a white solid (300 mg, 95% yield). LCMS m/e: 625.2 (M+H), 623.2 (M−H).

Workup

  1. temperaturethe solution was heated to 100 C in a sealed tube
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-2ac7af7a001547f6b88917f528319fc2
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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