1,2-Dichloroethane → Ethyl 3-(3-chloro-5-{5-[3-chloro-4-(propyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

HRID 423354Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH3:14])[C:5]([OH:7])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([C:39]([NH:41]O)=[NH:40])[CH:37]=2)[N:32]([CH2:43][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:31]=1>CN(C=O)C>[Cl:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([C:39]3[N:40]=[C:5]([C:4]4[CH:8]=[CH:9][C:10]([O:11][CH2:12][CH2:13][CH3:14])=[C:2]([Cl:1])[CH:3]=4)[O:7][N:41]=3)[CH:37]=2)[N:32]([CH2:43][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:31]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-Chloro-4-(propyloxy)benzoic acid (D100) (150 mg, 0.70 mmol) stirring in DMF was treated with EDC (146 mg, 0.76 mmol) followed by HOBt (104 mg, 0.76 mmol). The resultant solution was stirred and ethyl 3-{3-chloro-5-[(hydroxyamino)(imino)methyl]-1H-indol-1-yl}propanoate (D96) (216 mg, 0.70 mmol) added. Heated mixture at 80° C. until reaction was complete. Work up obtained the title compound as 160 mg of pale cream solid. δH (400 MHz, d6-DMSO) 1.03 (3H, t), 1.10 (3H, t), 1.77-1.86 (2H, m), 2.90 (2H, t), 4.05 (2H, q), 4.18 (2H, t), 4.49 (2H, t), 7.40 (1H, d), 7.74 (1H, s), 7.81 (1H, d), 7.91 (1H, dd), 8.15 (1H, dd), 8.22-8.23 (2H, m). MS (ES) C24H2335Cl2N3O4 requires 487; found 488 (MH+).

Workup

customuntil reaction

Sources & evidence

ORD record: ord-5373a5709e1f4ee78e71b20e943dbd1d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101775B2

Reaction notes

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