Water → HCID 136104188, compound

HRID 2088683Notes

Reaction equation

HRID 2088683 reaction equation
C([O:3][C:4](=O)[NH:5]/[C:6](/[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[Cl:17])=[CH:7]\[C:8]#[N:9])C.[CH3:19][CH:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]([NH:30][NH2:31])=O)[CH2:24][CH2:23]1)[CH3:21].O>CN1CCCC1=O>[Cl:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[C:6]1[NH:5][C:4](=[O:3])[N:31]2[N:30]=[C:28]([CH:25]3[CH2:26][CH2:27][N:22]([CH:20]([CH3:21])[CH3:19])[CH2:23][CH2:24]3)[N:9]=[C:8]2[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 583059791-(Propan-2-yl)piperidine-4-carbohydrazideHCID 58306026Ethyl[(Z)-1-(2-chloro-4-fluorophenyl)-2-cyanoethenyl]carbamate

Product 1

HCID 136104188HCID 136104188, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

1.5 g (5.14 mmol) of ethyl[(Z)-1-(2-chloro-4-fluorophenyl)-2-cyanoethenyl]carbamate (Example 36A) and 952 mg (5.14 mmol) of 1-(propan-2-yl)piperidine-4-carbohydrazide (Example 38A) were dissolved in 27 ml of N-methylpyrrolidone, and the mixture was stirred under argon at an oil bath temperature of 160° C. in a flask with fitted calcium chloride drying tube for 3 h. The reaction mixture was cooled to RT, water (50 ml) was added and the mixture was stirred for 15 min. The resulting precipitate was filtered off, washed with a little water and then dried under high vacuum. This gave 1.25 g (61% of theory) of the product.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. stirringthe mixture was stirred for 15 min
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with a little water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-22d7e7ac01a647c1a78112a0e349c58c
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

Loading…