Hydrazine hydrate (1:1) → HCID 73505014, compound

HRID 590824Notes

Reaction equation

HRID 590824 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH2:10][O:11][CH3:12])[N:5]=[C:4]([NH:13][C:14]([NH:16][C@@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])=[O:15])[CH:3]=1.O.[NH2:26][NH2:27]>CCO>[NH2:9][C:8]1[C:7]2[C:6]([CH2:10][O:11][CH3:12])=[N:5][C:4]([NH:13][C:14]([NH:16][C@@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])=[O:15])=[CH:3][C:2]=2[NH:27][N:26]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 118271819HCID 118271819, compound

Product 1

HCID 73505014HCID 73505014, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (R)-1-(4-chloro-5-cyano-6-(methoxymethyl)pyridin-2-yl)-3-(1-phenylethyl)urea (151.4 mg, 0.439 mmol) and hydrazine hydrate (75 μl, 1.546 mmol) in EtOH (4 ml) was heated to 100° C. in a sealed vial for 18 hr. The mixture was concentrated in vacuo and purified via flash chromatography (0-20% MeOH/EtOAc) to provide (R)-1-(3-amino-4-(methoxymethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd for C17H21N6O2 [M+H]+ 341. found 341. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 11.60 (s, 1H), 8.97 (s, 1H), 7.33 (m, 4H), 7.22 (m, 1H), 7.14 (s, 1H), 5.35 (s, 2H), 4.85 (t, J=7.1, 1H), 4.65 (m, 2H), 3.31 (s, 3H, overlaps with H2O peak), 3.15 (d, J=5.1 Hz, 1H), 1.39 (d, J=7.1 Hz, 1H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified via flash chromatography (0-20% MeOH/EtOAc)

Sources & evidence

ORD record
ord-c907c771774146a8af78b340c48f8a92
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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