Methanol → ((S)-2-{7-[(3-Ethylureido)-methyl]-furo[2,3-g]indazol-1-yl}-1-methylethyl)-carbamic acid benzyl ester

HRID 1453903Notes

Reaction equation

HRID 1453903 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@@H:11]([CH3:27])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][C:23]([CH2:25][NH2:26])=[CH:22][C:20]3=2)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.[CH2:36]([N:38]=[C:39]=[O:40])[CH3:37].CO>C1COCC1.ClCCl>[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@@H:11]([CH3:27])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][C:23]([CH2:25][NH:26][C:39]([NH:38][CH2:36][CH3:37])=[O:40])=[CH:22][C:20]3=2)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 7912DiisopropylamineHCID 8022Ethyl isocyanateHCID 68858114[(S)-2-(7-Aminomethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl ester

Product 1

HCID 68856399((S)-2-{7-[(3-Ethylureido)-methyl]-furo[2,3-g]indazol-1-yl}-1-methylethyl)-carbamic acid benzyl esterYield 81.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 17, Step B (0.20 g, 0.53 mmol) in THF (4 mL) was added polymer supported di-isopropylamine (1.5 eq, 0.79 mmol, 0.22 g) and ethyl isocyanate (0.042 mL, 0.52 mmol); this mixture was stirred at room temperature for three hours followed by the addition of methanol (5 mL). Dichloromethane (15 mL) was added and the mixture was filtered, evaporation of the filtrate gave a solid (0.19 g) which was purified by chromatography (silica gel, hexane/ethyl acetate gradient) to give a white solid (0.14 g, 59%): LC/MS m/z 450 [M+H]+.

Workup

  1. filtrationthe mixture was filtered
  2. customevaporation of the filtrate

Sources & evidence

ORD record
ord-0c728be099814df8905f697f1bd9f192
Source dataset
uspto-grants-2009_01
Patent number
US07476687B2

Reaction notes

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