Isopropyl chloroformate → HCID 86680407, compound

HRID 1023165Notes

Reaction equation

HRID 1023165 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][C:8]2[O:12][C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.Cl[C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26]>N1C=CC=CC=1>[Cl:21][C:16]1[CH:15]=[C:14]([NH:13][C:11]2[O:12][C:8]([CH2:7][O:6][C:5]3[CH:22]=[CH:23][C:2]([NH:1][C:25](=[O:26])[O:27][CH:28]([CH3:30])[CH3:29])=[CH:3][CH:4]=3)=[N:9][N:10]=2)[CH:19]=[CH:18][C:17]=1[Cl:20]

Participants

4

Reactant 2

HCID 7917Isopropyl chloroformateHCID 86680405HCID 86680405, compound

Product 1

HCID 86680407HCID 86680407, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 5-((4-aminophenoxy)methyl)-N-(3,4-dichlorophenyl)-1,3,4-oxadiazol-2-amine (130 mg, 0.370 mmol) in pyridine (1 mL) at 0° C., isopropyl chloroformate (1 M solution in toluene, 0.370 mL, 0.370 mmol) was added and the reaction was stirred at room temperature overnight. Solvent was removed under vacuum. The residue was filtered and purified by preparative HPLC to obtain isopropyl (4-((5-((3,4-dichlorophenyl)amino)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)carbamate (0.03 g, 14%). 1H NMR: 400 MHZ, DMSO-d6: δ 1.24 (d, J=6.00 Hz, 6H), 4.87 (t, J=6.40 Hz, 1H), 5.26 (s, 2H), 6.99 (dd, J=2.40, 6.80 Hz, 2H), 7.39 (d, J=8.80 Hz, 1H), 7.47 (dd, J=2.80, 9.00 Hz, 1H), 7.61 (d, J=8.80 Hz, 1H), 7.88 (d, J=2.80 Hz, 1H), 9.40 (s, 1H), 11.00 (s, 1H). LCMS: RT 2.11 min. LCMS (ES-API), m/z 439.0 (M+H).

Workup

  1. customSolvent was removed under vacuum
  2. filtrationThe residue was filtered
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-06f06a1674f647928c19f2e2b98fb4fa
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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