Water → HCID 62269658, compound

HRID 578917Notes

Reaction equation

HRID 578917 reaction equation
Cl[C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)=[O:7])=[CH:4][N:3]=1.[NH2:20][NH2:21].O>C(O)(C)C>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:18]=[CH:19][C:2]([NH:20][NH2:21])=[N:3][CH:4]=2)=[CH:11][CH:12]=1)#[N:17]

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 60736795HCID 60736795, compound

Product 1

HCID 62269658HCID 62269658, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Combined 6-chloro-N-(4-cyanobenzyl)nicotinamide (500 mg, 1.840 mmol) and hydrazine (0.578 mL, 18.40 mmol) in isopropanol (5 mL) and heated at 90° C. for 5 h. The supernatant was decanted and concentrated in vacuo to give a white solid which was stirred vigorously with water (ca. 10 mL) for 2 hours, then was filtered and the solid dried to give the title compound (batch 1, 101 mg) as a pink solid. The fine solids from the reaction (after supernatant was removed) was stirred vigorously with water (ca. 10 mL) for 2 hours, then filtered and dried in the lyophilizer to give the title compound (batch 2, 179 mg) as a tan solid. Large solids from the reaction (after supernatant was removed) were crushed and stirred vigorously with water (10 mL) for 1 hour, then filtered and dried in the lyophilizer to give the title (batch 3, 135 mg) as a beige solid. The combined yield was 415 mg (84% yield). MS m/z 268 [M+H]+.

Workup

  1. customThe supernatant was decanted
  2. concentrationconcentrated in vacuo
  3. customto give a white solid which
  4. filtrationwas filtered
  5. customthe solid dried

Sources & evidence

ORD record
ord-0d96192af1d94eba8a334d21c1b22b19
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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