Diisopropylethylamine → HCID 178507987, compound

HRID 855666Notes

Reaction equation

HRID 855666 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[NH:10][N:11]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[CH:13]=2)[C:3]=1[N+:17]([O-])=O.C(OC([N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([NH2:36])[CH:34]=2)[C:29](=[O:37])[NH:28]1)=O)(C)(C)C.C(N(C(C)C)CC)(C)C>C1COCC1>[NH2:17][C:3]1[C:2]([NH:36][C:33]2[CH:34]=[C:35]3[C:30]([C:29](=[O:37])[NH:28][NH:27]3)=[CH:31][CH:32]=2)=[N:7][CH:6]=[N:5][C:4]=1[NH:8][C:9]1[NH:10][N:11]=[C:12]([CH:14]2[CH2:16][CH2:15]2)[CH:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 574980196-Amino-3-oxo-2,3-dihydro-indazole-1-carboxylic acid tert-butyl esterHCID 178526743HCID 178526743, compound

Product 1

HCID 178507987HCID 178507987, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6-chloro-5-nitro-pyrimidin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine (50 mg, 0.18 mmol) in anhydrous THF (2 mL) was added 6-amino-3-oxo-2,3-dihydro-indazole-1-carboxylic acid tert-butyl ester (67 mg, 0.27 mmol) and diisopropylethylamine (23 mg, 0.18 mmol). The mixture was stirred at RT for 14 hrs and the solvents were removed under vacuum. The residue was dissolved in CH2Cl2 (3 mL) and treated with TFA (2 mL) at RT for 2 hrs. After removal of the solvents via evaporation, the residue was reduced by hydrogen (50 psi) in MeOH (10 mL) in the presence of Pd/C (10%, 50 mg) for 3 hrs. The solution was filtered via celite, the filtrate was evaporated under vacuum, and the residue was purified by HPLC to give the desired product as white solid (22 mg). NMR (500 MHz, DMSO-d6) δ11.16 (br, 1H), 9.92 (br, 1H), 8.98 (s, 1H), 8.27 (s, 1H), 7.67 (s, 1H), 7.55 (d, 1H), 7.08 (d, 1H), 5.95 (s, 1H), 2.00 (m, 1H), 1.06 (m, 2H), 0.81 (m, 2H) ppm. MS (ES+): m/e=364.3 (M+H); LC/Method A/2.45 min.

Workup

  1. customthe solvents were removed under vacuum
  2. dissolutionThe residue was dissolved in CH2Cl2 (3 mL)
  3. additiontreated with TFA (2 mL) at RT for 2 hrs
  4. customAfter removal of the solvents
  5. customvia evaporation
  6. waitthe residue was reduced by hydrogen (50 psi) in MeOH (10 mL) in the presence of Pd/C (10%, 50 mg) for 3 hrs
  7. filtrationThe solution was filtered via celite
  8. customthe filtrate was evaporated under vacuum
  9. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-9d356d116cf441a2b5b2d146b8f89199
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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