Toluene → HCID 58204820, compound

HRID 1629312Notes

Reaction equation

HRID 1629312 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13]([C:15]([NH2:17])=O)[N:14]=[C:7]3[C:6]=2[CH:18]=1.CO[C:21](OC)([N:23](C)C)[CH3:22].C1(C)C=CC=CC=1.Cl.[CH:36]([NH:39]N)([CH3:38])[CH3:37]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13]([C:15]4[N:39]([CH:36]([CH3:38])[CH3:37])[N:23]=[C:21]([CH3:22])[N:17]=4)[N:14]=[C:7]3[C:6]=2[CH:18]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 855731-Isopropylhydrazine hydrochlorideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 58204450HCID 58204450, compound

Product 1

HCID 58204820HCID 58204820, compoundYield 26%

Conditions

Temperature
95 °C

Procedure

10-Fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide from Example 90 (0.2 g, 0.81 mmol), dimethylacetamide-dimethyacetal (0.36 mL, 2.4 mmol), and toluene (10 mL, 90 mmol) were combined in a round bottom flask with a vigreux condensation column attached. Heated at 95° C. for more than 24 hours and concentrated in vacuo. The residue was dissolved in acetic acid and isopropylhydrazine hydrochloride (0.11 g, 0.97 mmol) was added and heated at 95° C. with a vigreux condensation column attached for four hours. Complete reaction by LCMS. Concentrated in vacuo and purified by HPLC to give 281 (67.7 mg, 26% yield, M+1 328.1)

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in acetic acid
  3. temperatureheated at 95° C. with a vigreux condensation column
  4. customComplete reaction by LCMS
  5. concentrationConcentrated in vacuo
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-c1f9cda3a7e0412d90d6649e36943c5c
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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