Ammonia → HCID 22063482, compound

HRID 1666161Notes

Reaction equation

HRID 1666161 reaction equation
C(O[CH:9]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[C:19]([C:20](=[O:26])[CH:21](OCC)O)[C:11]=2[O:10]1)C1C=CC=CC=1.[CH:27]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([NH2:40])([CH3:39])[CH3:38])=[CH:32][CH:31]=1)([CH3:29])[CH3:28].[BH4-].[Na+].Cl.N>C(O)C.CC(C)=O.C(OCC)(=O)C.O>[CH2:20]([O:26][C:17]1[CH:18]=[C:19]([CH:20]([OH:26])[CH2:21][NH:40][C:37]([CH3:38])([CH3:39])[CH2:36][C:33]2[CH:32]=[CH:31][C:30]([CH:27]([CH3:29])[CH3:28])=[CH:35][CH:34]=2)[C:11]2[O:10][CH2:9][C:14](=[O:15])[NH:13][C:12]=2[CH:16]=1)[C:19]1[CH:11]=[CH:12][CH:16]=[CH:17][CH:18]=1

Participants

10

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22063456HCID 22063456, compoundHCID 22063484HCID 22063484, compound

Product 1

HCID 22063482HCID 22063482, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.18 g (6.1 mmol) of benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 1.1 g (5.8 mmol) of 2-(4-isopropylphenyl)-1,1-dimethylethylamine are stirred in 40 mL ethanol at 50° C.-80° C. for one hour. After cooling to ambient temperature, 0.24 g (6.3 mmol) sodium borohydride is added. The mixture is stirred for one hour, diluted with 5 mL acetone, and stirred for a further 30 minutes. The reaction mixture is acidified with hydrochloric acid, combined with 100 mL water and 80 mL ethyl acetate, and made alkaline with ammonia. The organic phase is separated off, dried with sodium sulfate, and freed from solvent. The residue is dissolved in 20 mL ethyl acetate and 10 mL water, acidified with concentrated hydrochloric acid and diluted with diethyl ether. After the addition of a crystallization aid, the solid precipitate is suction filtered and washed. White solid. Yield: 1.7 g (52%, hydrochloride); melting point: 220° C.-222° C.

Workup

  1. stirringstirred for a further 30 minutes
  2. customThe organic phase is separated off
  3. dry with materialdried with sodium sulfate
  4. dissolutionThe residue is dissolved in 20 mL ethyl acetate
  5. additiondiluted with diethyl ether
  6. additionAfter the addition of a crystallization aid
  7. filtrationfiltered
  8. washwashed

Sources & evidence

ORD record
ord-5014b6fc3bbd42f587dee11b16f1b5cf
Source dataset
uspto-grants-2011_10
Patent number
US08044046B2

Reaction notes

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