1,2-Dichloroethane → 1,1-Dimethylethyl 9-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 1514229Notes

Reaction equation

HRID 1514229 reaction equation
[OH:1][NH:2][C:3](=[NH:22])[C:4]1[C:14]2[O:13][CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[O:33][CH:34]([CH3:36])[CH3:35])[C:27](O)=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O.O>[Cl:23][C:24]1[CH:25]=[C:26]([C:27]2[O:1][N:2]=[C:3]([C:4]3[C:14]4[O:13][CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:9][C:8]=4[CH:7]=[CH:6][CH:5]=3)[N:22]=2)[CH:30]=[CH:31][C:32]=1[O:33][CH:34]([CH3:35])[CH3:36]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acidHCID 178452412HCID 178452412, compound

Product 1

HCID 594034901,1-Dimethylethyl 9-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylateYield 40.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 1,1-dimethylethyl 9-[(hydroxyamino)(imino)methyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 65) (500 mg, 1.627 mmol), 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (384 mg, 1.790 mmol), EDC (468 mg, 2.440 mmol) and HOBT (299 mg, 1.952 mmol) in DMF (5 ml) was stirred at RT overnight then heated at 120° C. for 3 hrs. The reaction mixture was cooled, diluted with EtOAc/water and the organics dried over magnesium sulfate and evaporated. Purified by flash chromatography eluting with EtOAc/iso-hexane 1:3 to give the title compound (320 mg) as a white solid. MS (ES): C25H2835ClN3O5 requires 485; found 486 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. dry with materialthe organics dried over magnesium sulfate
  3. customevaporated
  4. customPurified by flash chromatography
  5. washeluting with EtOAc/iso-hexane 1:3

Sources & evidence

ORD record
ord-bdd65fcee692465297e8e6ec83a46e3a
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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