Hydrazine → HCID 86681457, compound

HRID 339964Notes

Reaction equation

HRID 339964 reaction equation
[F: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[F: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 86681456HCID 86681456, compound

Product 1

HCID 86681457HCID 86681457, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[(2S)-2-[5-(4-fluoro-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, 0.058 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 8.1 mg of the desired product as white solid. LC/MS found: 383.0 (M+1)+; 1H NMR (400 MHz, DMSO-d6) δ ppm: 7.73 (d, J=7.8 Hz, 1H), 7.71 (s, 1H), 7.61 (d, J=4.9 Hz, 1H), 7.57 (d, J=7.9 Hz, 1H), 7.23 (ddd, J1=8.2 Hz, J2=7.8 Hz, J3=6.4 Hz, 1H), 7.03 (m, 2H), 6.93 (dddd, J1=8.6 Hz, J2=8.4 Hz, J3=2.6 Hz, J4=0.8 Hz, 1H), 4.48 (s, 2H), 4.42 (m, 1H), 3.79 (s, 3H), 3.05 (dd, J1=14.40 Hz, J2=5.20 Hz, 1H), 2.88 (dd, J1=14.40 Hz, J2=10.00 Hz, 1H), 2.81 (d, J=6.70 Hz, 2H).

Workup

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

Sources & evidence

ORD record
ord-470ab0e1e6784c669902fd47ce94f331
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

Loading…