Hydrazine → HCID 86681459, compound

HRID 339966Notes

Reaction equation

HRID 339966 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH3:38])[C:6]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([C@@H:17]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1)[CH2:18][N:19]1C(=O)C3C(=CC=CC=3)C1=O)[CH2:10]2.NN>CO.O1CCCC1>[NH2:19][CH2:18][C@@H:17]([N:11]1[CH2:10][C:9]2[C:13](=[CH:14][CH:15]=[C:7]([C:6]3[N:5]([CH3:38])[N:4]=[CH:3][C:2]=3[Br:1])[CH:8]=2)[C:12]1=[O:16])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 86681458HCID 86681458, compound

Product 1

HCID 86681459HCID 86681459, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[(2S)-2-[5-(4-bromo-1-methyl-1H-pyrazol-5-yl)-1-oxo-1,3-dihydro-2H-isoindol-2-yl]-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione (30.0 mg, 0.0523 mmol) and hydrazine (0.2 mL, 6 mmol) in methanol (1.0 mL) and tetrahydrofuran (1.0 mL) was stirred at room temperature overnight. Direct purification on prep.—HPLC (pH=10) gave 7.8 mg of the desired product as white solid. LC/MS found: 443.0 (M+1)+; 1H NMR (400 MHz, DMSO-d6) δ: 7.74 (d, J=7.60 Hz, 1H), 7.68 (m, 2H), 7.54 (dd, J1=8.00 Hz, J2=1.60 Hz, 1H), 7.24 (m, 1H), 7.05 (m, 2H), 6.95 (dt, J1=8.40 Hz, J2=2.00 Hz, 1H), 4.49 (d, J=2.80 Hz, 2H), 4.42 (m, 1H), 3.76 (s, 3H), 3.04 (dd, J1=14.00 Hz, J2=5.20 Hz, 1H), 2.90 (dd, J1=14.40 Hz, J2=9.60 Hz, 1H), 2.81 (d, J=6.80 Hz, 2H).

Workup

  1. customDirect purification on prep.—HPLC (pH=10)

Sources & evidence

ORD record
ord-95ebc9dc9281465bb8c8527fdbf5baef
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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