Hydrazine → HCID 66745493, compound

HRID 1959439Notes

Reaction equation

HRID 1959439 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:17]2[CH2:22][CH2:21][N:20]([S:23]([CH2:26][CH2:27][N:28]3C(=O)C4C(=CC=CC=4)C3=O)(=[O:25])=[O:24])[CH2:19][CH:18]=2)=[N:6][C:7]=1[C:8]1[NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]=1.NN>C(O)C.CS(C)=O>[NH2:28][CH2:27][CH2:26][S:23]([N:20]1[CH2:19][CH:18]=[C:17]([C:5]2[N:6]=[C:7]([C:8]3[NH:12][C:11]4[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=4[N:9]=3)[C:2]([NH2:1])=[N:3][CH:4]=2)[CH2:22][CH2:21]1)(=[O:25])=[O:24]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 66745418HCID 66745418, compound

Product 1

HCID 66745493HCID 66745493, compoundYield 22.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-(2-(4-(5-amino-6-(1H-benzo[d]imidazol-2-yl)pyrazin-2-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)ethyl)isoindoline-1,3-dione (24 mg, 0.045 mmol) in ethanol (240 μL) was added hydrazine (1.5 mg, 1.4 μL, 0.045 mmol), and the reaction mixture was heated at 80° C. for 2 h. The reaction mixture was cooled to room temperature and was dissolved in 0.5 ml of DMSO and purified via reverse phase HPLC using 1 to 99% MeOH in H2O 2O (0.05% HCl as modifier) to obtain 5-(1-(2-aminoethylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-3-(1H-benzo[d]imidazol-2-yl)pyrazin-2-amine (4 mg, 18%). 1HNMR (400 MHz, MeOD) δ 8.59 (s, 1H), 8.12-8.03 (m, 2H), 7.78 (dd, J=6.1, 3.2 Hz, 2H), 7.16 (s, 1H), 4.43 (d, J=2.1 Hz, 2H), 3.95 (t, J=5.6 Hz, 2H), 3.81-3.67 (m, 4H), 3.12 (s, 2H). LC/MS m/z 400.0 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompurified via reverse phase

Sources & evidence

ORD record
ord-5ecd7543b83d4a038aa2d1933293138d
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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