Hydrazine → HCID 59332534, compound

HRID 1640937Notes

Reaction equation

HRID 1640937 reaction equation
NN.[N:3]1([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[S:21][C:20]4[C:22]([C:26]5[CH:31]=[C:30]([F:32])[N:29]=[CH:28][C:27]=5[O:33][CH2:34][CH2:35][N:36]5C(=O)C6C(=CC=CC=6)C5=O)=[CH:23][CH:24]=[CH:25][C:19]=4[CH:18]=3)[C:14]([F:47])=[CH:13][N:12]=2)[CH:7]=[CH:6][N:5]=[N:4]1>C(O)C>[N:3]1([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[S:21][C:20]4[C:22]([C:26]5[C:27]([O:33][CH2:34][CH2:35][NH2:36])=[CH:28][N:29]=[C:30]([F:32])[CH:31]=5)=[CH:23][CH:24]=[CH:25][C:19]=4[CH:18]=3)[C:14]([F:47])=[CH:13][N:12]=2)[CH:7]=[CH:6][N:5]=[N:4]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 66738405HCID 66738405, compound

Product 1

HCID 59332534HCID 59332534, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Add hydrazine (0.03 mL, 0.8 mmol) to a solution of 2-(2-(4-(2-(2-(2-(1H-1,2,3-triazol-1-yl)ethylamino)-5-fluoropyrimidin-4-yl)benzo[b]thiophen-7-yl)-6-fluoropyridin-3-yloxy)ethyl)isoindoline-1,3-dione (0.25 g, 0.4 mmol) in ethanol (5 mL). Stir the mixture at 40° C. overnight. Remove the solvent and purify the residue by column chromatography (10% methanol in DCM) to afford the title compound (70 mg, 35%). MS (ES) m/z 495 [M+1]+.

Workup

  1. customRemove the solvent
  2. custompurify the residue by column chromatography (10% methanol in DCM)

Sources & evidence

ORD record
ord-2d465e4c2e4f4d39a73411500e1ba95b
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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