1-(3-Amino-3-methylbutyl)-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one → 1-{3-[2-(7-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-hydroxyethylamino]-3-methylbutyl}-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one

HRID 1867326Notes

Reaction equation

HRID 1867326 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[C:11]([CH:20]2[CH2:22][O:21]2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][C:24]([CH3:43])([CH3:42])[CH2:25][CH2:26][N:27]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[C:30]([CH2:39][CH3:40])([CH2:37][CH3:38])[O:29][C:28]1=[O:41]>C(O)(C)C.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[C:11]([CH:20]([OH:21])[CH2:22][NH:23][C:24]([CH3:43])([CH3:42])[CH2:25][CH2:26][N:27]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[C:30]([CH2:39][CH3:40])([CH2:37][CH3:38])[O:29][C:28]2=[O:41])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 210728171-(3-Amino-3-methylbutyl)-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-oneHCID 574693717-benzyloxy-5-oxiranyl-1H-quinolin-2-one

Product 1

HCID 210728131-{3-[2-(7-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-hydroxyethylamino]-3-methylbutyl}-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 7-benzyloxy-5-oxiranyl-1H-quinolin-2-one (112 mg, 0.382 mmol) and 1-(3-amino-3-methylbutyl)-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one (220 mg, 0.758 mmol) in isopropanol (1.0 mL) is heated in the microwave for 1 hour to 135° C. The mixture is diluted with EtOAc (10 mL) and washed with 0.5 M aqueous tartaric acid solution, whereupon half the product is precipitated. The phases are separated and the aqueous suspension is combined with MeOH until a clear solution is obtained again. The aqueous phase is extracted with dichloromethane and the combined organic phases are dried with sodium sulfate and evaporated down in vacuo. The residue is stirred with EtOAc and the precipitate is filtered off and dried in vacuo. Yield: 152 mg (68%); HPLC-MS: Rt=14.8 min. (method A).

Workup

  1. temperatureis heated in the microwave for 1 hour to 135° C
  2. washwashed with 0.5 M aqueous tartaric acid solution, whereupon half the product
  3. customis precipitated
  4. customThe phases are separated
  5. customis obtained again
  6. extractionThe aqueous phase is extracted with dichloromethane
  7. dry with materialthe combined organic phases are dried with sodium sulfate
  8. customevaporated down in vacuo
  9. filtrationthe precipitate is filtered off
  10. customdried in vacuo

Sources & evidence

ORD record
ord-9322cea089394c38bf307482b224dfef
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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