Water → HCID 73504799, compound

HRID 590821Notes

Reaction equation

HRID 590821 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([C:12]#[N:13])=[C:10](Cl)[CH:9]=[C:8]([NH:15][C:16]([NH:18][C@@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])=O)[N:7]=1)(=O)C.[NH2:27][NH2:28].[OH2:29]>C(O)C>[NH2:13][C:12]1[C:11]2[C:6]([CH2:5][OH:4])=[N:7][C:8]([NH:15][C:16]([NH:18][C@@H:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH3:20])=[O:29])=[CH:9][C:10]=2[NH:28][N:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 118272458HCID 118272458, compound

Product 1

HCID 73504799HCID 73504799, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (R)-(4-chloro-3-cyano-6-(3-(1-phenylethyl)ureido)pyridin-2-yl)methyl acetate (59.1 mg, 0.159 mmol) in ethanol (2 ml) was charged with hydrazine, H2O (46 μl, 0.948 mmol), sealed and heated to 100° C. for 14.5 hr. The mixture was concentrated in vacuo and the residue was purified via flash chromatography (0-20% MeOH/DCM, then 0-20% MeOH/EtOAc) to provide (R)-1-(3-amino-4-(hydroxymethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. For C16H19N6O2 [M+H]+ 327. found 327. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 11.51 (s, 1H), 8.91 (s, 1H), 7.33 (m, 5H), 7.22 (m, 1H), 6.00 (t, J=5.6 Hz, 1H), 5.60 (s, 2H), 4.84 (m, 1H), 4.67 (d, J=5.6, 2H), 1.39 (d, J=7.1 Hz, 3H).

Workup

  1. customsealed
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified via flash chromatography (0-20% MeOH/DCM

Sources & evidence

ORD record
ord-83036b98ee534902948181de6b63a336
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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