Water → HCID 90015121, compound

HRID 1484502Notes

Reaction equation

HRID 1484502 reaction equation
C1(O[C:8](=[O:29])[NH:9][C:10]2[CH:11]=[N:12][C:13]([O:16][C:17]3[C:22]4[C:23]([CH3:27])([CH3:26])[CH2:24][O:25][C:21]=4[C:20]([CH3:28])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)C=CC=CC=1.O.[NH2:31][NH2:32].O>O1CCOCC1>[CH3:26][C:23]1([CH3:27])[C:22]2[C:17]([O:16][C:13]3[N:12]=[CH:11][C:10]([NH:9][C:8]([NH:31][NH2:32])=[O:29])=[CH:15][CH:14]=3)=[CH:18][CH:19]=[C:20]([CH3:28])[C:21]=2[O:25][CH2:24]1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 118028968HCID 118028968, compound2×

Product 1

HCID 90015121HCID 90015121, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl{6-[(3,3,7-trimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}carbamate (Intermediate 1, 640 mg, 1.64 mmol) was dissolved in dioxane (7 mL) and hydrazine monohydrate (8.2 mmol) was added. The reaction mixture was stirred for 30 minutes at room temperature and then at 70° C. for 1 hour. Water was added and the resulting suspension was stirred for 1 hour and then filtered. The solid was collected, washed with water and dried under vacuum at 25° C. affording the title compound (340 mg) as off-white solid.

Workup

  1. waitat 70° C. for 1 hour
  2. stirringthe resulting suspension was stirred for 1 hour
  3. filtrationfiltered
  4. customThe solid was collected
  5. washwashed with water
  6. customdried under vacuum at 25° C.

Sources & evidence

ORD record
ord-7976457c606b4cdfb4586356fb880fdb
Source dataset
uspto-grants-2016_08
Patent number
US09422252B2

Reaction notes

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