Hydrazine hydrate (1:1) → HCID 68485833, compound

HRID 336506Notes

Reaction equation

HRID 336506 reaction equation
[CH:1]1([NH:6][C:7]2[CH:8]=[C:9]([CH2:23][N:24]3C(=O)C4C(=CC=CC=4)C3=O)[CH:10]=[C:11]3[C:15]=2[NH:14][C:13]([C:16]2[S:17][CH2:18][C@@H:19]([CH2:21][OH:22])[N:20]=2)=[CH:12]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.NN>C(O)C>[NH2:24][CH2:23][C:9]1[CH:10]=[C:11]2[C:15](=[C:7]([NH:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:8]=1)[NH:14][C:13]([C:16]1[S:17][CH2:18][C@@H:19]([CH2:21][OH:22])[N:20]=1)=[CH:12]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68485274HCID 68485274, compound

Product 1

HCID 68485833HCID 68485833, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2-[7-Cyclopentylamino-2((R)-4-hydroxymethyl-4,5-dihydro-thiazol-2-yl)-1H -indol-5-ylmethyl]-isoindol-1,3-dione (27 mg, 0.07 mmol) prepared in Example 64 was dissolved in ethanol (3 mL). Hydrazine hydrate (0.6 mL, 0.11 mmol) was added thereto, and the mixture was stirred for 3 h at 80° C. After completion of the reaction, the reaction mixture was distilled under reduced pressure, and purified by column chromatography to give the title compound (7 mg, Yield 37%).

Workup

  1. customAfter completion of the reaction
  2. distillationthe reaction mixture was distilled under reduced pressure
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-62281922606643699ca09b8fbba5ab98
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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