1,2-Dichloroethane → HCID 59403528, compound

HRID 1514200Notes

Reaction equation

HRID 1514200 reaction equation
[OH:1][NH:2][C:3](=[NH:22])[C:4]1[CH:21]=[CH:20][C:7]2[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11][O:12][C:6]=2[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>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[CH:21]=[CH:20][C:7]4[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:10][CH2:11][O:12][C:6]=4[CH:5]=3)[N:22]=2)[CH:30]=[CH:31][C:32]=1[O:33][CH:34]([CH3:35])[CH3:36]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acidHCID 178452417HCID 178452417, compound

Product 1

HCID 59403528HCID 59403528, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

A mixture of 1,1-dimethylethyl 8-[(hydroxyamino)(imino)methyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 33) (0.195 g, 0.634 mmol), 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (Preparation 6) (0.136 g, 0.634 mmol), EDC (0.146 g, 0.761 mmol) and HOBT (0.107 g, 0.698 mmol) DMF (4 ml) was stirred at room temperature for 20 minutes then heated at 100° C. for 17 hours. The cooled reaction mixture was diluted with EtOAc/water (40 ml of each) and the organics collected, dried (magnesium sulphate), evaporated and purified by biotage chromatography in 1:4 EtOAc/iso-hexane to give the title compound (172 mgs) as a white solid. MS (ES) C25H2835ClN3O5 requires 485; found 486 [M+H]+; C25H2837ClN3O5 requires 487; found 488 [M+H]+.

Workup

  1. temperaturethen heated at 100° C. for 17 hours
  2. customThe cooled reaction mixture
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated
  5. custompurified by biotage chromatography in 1:4 EtOAc/iso-hexane

Sources & evidence

ORD record
ord-02ecfd3f5228449db1d197697500d59b
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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