Water → HCID 59285862, compound

HRID 1011583Notes

Reaction equation

HRID 1011583 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[NH2:18][C:19]([NH:21][C:22]1[NH:23][C:24]([C:30]2[CH:35]=[CH:34][C:33]([C:36](OCC)=[O:37])=[CH:32][CH:31]=2)=[CH:25][C:26]=1[C:27]([NH2:29])=[O:28])=[O:20].O>O1CCCC1.CO>[NH2:18][C:19]([NH:21][C:22]1[NH:23][C:24]([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][OH:37])=[CH:32][CH:31]=2)=[CH:25][C:26]=1[C:27]([NH2:29])=[O:28])=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 21225700Diisobutylaluminumhydride2×HCID 25006450HCID 25006450, compound

Product 1

HCID 59285862HCID 59285862, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, 1.0M diisobutylaluminum hydride in toluene solution (3.2 mL, 3.2 mmol) was added to a solution of 2-aminocarbonylamino-5-(4-ethoxycarbonylphenyl)pyrrole-3-carboxamide (Compound No. 1-30, 0.28 g, 0.89 mmol) in anhydrous tetrahydrofuran (5 mL) and the mixture was stirred for 2 hours. Moreover, 1.0M diisobutylaluminum hydride in toluene solution (3.2 mL, 3.2 mmol) was added thereto and the whole was stirred for 2 hours, and then water (2 mL) and methanol (2 mL) were added thereto. The mixture was filtered with celite with 1,4-dioxane (10 mL) and the filtrate was concentrated in vacuo. The obtained solid was washed with diethyl ether (2 mL), dried under reduced pressure to give the target compound (0.16 g) as a pale yellow solid (Yield 66%).

Workup

  1. temperatureUnder ice-cooling
  2. filtrationThe mixture was filtered with celite with 1,4-dioxane (10 mL)
  3. concentrationthe filtrate was concentrated in vacuo
  4. washThe obtained solid was washed with diethyl ether (2 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-ad32c24f1e1d4ef18ebf15a4c0261c5c
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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