Hydrazine → HCID 66780434, compound

HRID 1958057Notes

Reaction equation

HRID 1958057 reaction equation
NN.[CH3:3][C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:14][N:15]1[C:20]2[N:21]=[C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[S:23][C:19]=2[C:18](=[O:30])[N:17]=[C:16]1[CH2:31][N:32]1C(=O)C2C(=CC=CC=2)C1=O>CO>[NH2:32][CH2:31][C:16]1[N:15]([CH2:14][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([F:11])([F:13])[F:12])[C:4]=2[CH3:3])[C:20]2[N:21]=[C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[S:23][C:19]=2[C:18](=[O:30])[N:17]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 66780004HCID 66780004, compound

Product 1

HCID 66780434HCID 66780434, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine (3.31 μL, 0.105 mmol) was added to a solution of 2-{[4-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-2-(4-morpholinyl)-7-oxo-4,7-dihydro[1,3]thiazolo[4,5-d]pyrimidin-5-yl]methyl}-1H-isoindole-1,3(2H)-dione (60 mg, 0.105 mmol) in Methanol (2 mL). The mixture was stirred at RT for 2 hours. The solvent was removed and the residue was purified by reverse phase HPLC (10% org˜50% org) to give the titled product 16 mg (35%). LC/MS (ES) m/z 440.1 (M+H)+, 1H NMR (400 MHz, DMSO-d6) δ ppm 8.30 (br, s, 2H), 7.67 (m, 1H), 7.38 (m, 1H), 6.87 (m, 1H), 5.58 (s, 2H), 4.20 (m, 2H), 3.66 (m, 4H), 3.56 (m, 4H), 2.37 (s, 3H)

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by reverse phase HPLC (10% org˜50% org)

Sources & evidence

ORD record
ord-8b003ceb03724ceba47bcc0dbd090769
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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