N-methyl-2-pyrrolidone → HCID 57513756, compound

HRID 2368431Notes

Reaction equation

HRID 2368431 reaction equation
CN1C(=O)CCC1.[CH2:8]([N:15]1[C:19]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[N:18][C:17]([NH2:27])=[N:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[O:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[N:39]=2)=[CH:31][CH:30]=1>CCOC(C)=O>[CH2:8]([N:15]1[C:19]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[N:18][C:17]([NH:27][C:37]([C:38]([NH:39][C:35](=[O:36])[C:32]2[CH:31]=[CH:30][C:29]([F:28])=[CH:34][CH:33]=2)([CH3:41])[CH3:40])=[O:42])=[N:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 13707964HCID 13707964, compoundHCID 57435373HCID 57435373, compound

Product 1

HCID 57513756HCID 57513756, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 5 mL Biotage microwave vial were added NMP (1 ml), 1-benzyl-5-(4-fluorophenyl)-1H-1,2,4-triazol-3-amine (150 mg, 0.559 mmol), 2-(4-fluorophenyl)-4,4-dimethyloxazol-5(4H)-one (116 mg, 0.559 mmol,), under N2. Then it was placed in 100° C. oil bath and stirred for 2.5 h. It was cooled to r.t. and diluted with 2 ml of EtOAc. It was stirred for 10 min that resulted precipitation of the desired product. Then 2 mL of water was added and it was stirred for additional 10 min followed by addition of a couple drops of heptane. The precipitates were collected by filtration and dried under vacuum overnight. This afforded the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) 1.50 (s, 6H) 5.40 (s, 2H) 7.08-7.14 (m, 2H) 7.24-7.39 (m, 7H) 7.63-7.71 (m, 2H) 7.96-8.04 (m, 2H) 8.33 (s, 1H) 10.17 (s, 1H). MS (m/z) 476.2 M(+1), tR=1.36, Method A.

Workup

  1. customwas placed in 100° C.
  2. stirringIt was stirred for 10 min that
  3. customresulted
  4. customprecipitation of the desired product
  5. additionThen 2 mL of water was added
  6. stirringit was stirred for additional 10 min
  7. additionfollowed by addition of a couple drops of heptane
  8. filtrationThe precipitates were collected by filtration
  9. customdried under vacuum overnight

Sources & evidence

ORD record
ord-822f9b5159ba4c1c8611bc2836bb7b1f
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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