Water → HCID 68501896, compound

HRID 1176603Notes

Reaction equation

HRID 1176603 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:11]=[CH:10][C:9]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:19])[CH2:14][CH:13]3[O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]4[O:38][CH2:37][C:36](=[O:39])[N:35]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[C:34]=4[CH:45]=3)=[CH:8][CH:7]=2)[CH2:2]1.Cl[C:47]1[S:48][C:49]2[CH:55]=[CH:54][CH:53]=[CH:52][C:50]=2[N:51]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C>[S:48]1[C:49]2[CH:55]=[CH:54][CH:53]=[CH:52][C:50]=2[N:51]=[C:47]1[N:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:11]=[CH:10][C:9]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[O:19])[CH2:14][CH:13]3[O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]4[O:38][CH2:37][C:36](=[O:39])[N:35]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[C:34]=4[CH:45]=3)=[CH:8][CH:7]=2)[CH2:2]1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 119872-ChlorobenzothiazoleHCID 68497806HCID 68497806, compound

Product 1

HCID 68501896HCID 68501896, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 0.835 g of benzyl 4-[4-(azetidin-3-yloxy)phenyl]-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate (Example 257c) and 0.233 g of 2-chlorobenzothiazole in 16 ml of N,N-dimethylformamide is admixed with 0.345 g of potassium carbonate. The mixture is stirred at 150° C. over 1 hour, cooled to room temperature and poured onto a mixture of 100 ml of brine, 50 ml of water and 150 ml of ethyl acetate. The phases are separated and the aqueous phase is extracted with 150 ml of ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a light yellow resin from the residue by means of flash chromatography (SiO2 60F). Rf=0.35 (4:1 EtOAc-heptane); Rt=4.78.

Workup

  1. temperaturecooled to room temperature
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with 150 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-19de62b00af04084b8a586f464470ef1
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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