Ethanol → HCID 69157686, compound

HRID 899646Notes

Reaction equation

HRID 899646 reaction equation
C(OC(N1C2C=CC=CC=2N=C1CN(C[C:30](=C)[CH2:31][CH2:32][N:33]1[C:41](=[O:42])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]1=[O:43])C1C2N=CC=CC=2CCC1)=O)(C)(C)C.O.NN.[CH2:48]([OH:50])[CH3:49]>>[OH:50][CH2:48][CH2:49][C:31](=[CH2:30])[CH2:32][N:33]1[C:34](=[O:43])[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:41]1=[O:42]

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 69178437HCID 69178437, compound

Product 1

HCID 69157686HCID 69157686, compoundYield 55%

Procedure

To a solution of 2-{[[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-methylene-butyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzimidazole-1-carboxylic acid tert-butyl ester (0.239 g, 0.40 mmol) in ethanol (8 mL) was added hydrazine monohydrate (0.40 mL, 8.26 mmol) and the resultant mixture was stirred at room temperature overnight. The mixture was filtered through filter paper and concentrated. Purification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2—CH3OH—NH4OH) provided 86 mg (55%) of the free base of the title compound as a yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthrough filter paper
  3. concentrationconcentrated
  4. customPurification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-8befa38767084b6a9ed19523ddef1bb1
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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