Hydrazine → (S)-1-(5-(4-chlorophenyl)oxazol-2-yl)ethanamine

HRID 57388Notes

Reaction equation

NN.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C@@H:15]([N:17]3C(=O)C4C(=CC=CC=4)C3=O)[CH3:16])=[N:12][CH:11]=2)=[CH:6][CH:5]=1>C(O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:14][C:13]([C@@H:15]([NH2:17])[CH3:16])=[N:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Hydrazine (0.55 ml, 6.09 mmol) was added to a solution of (S)-2-(1-(5-(4-chlorophenyl)oxazol-2-yl)ethyl)isoindoline-1,3-dione (430 mg, 1.219 mmol) in ethanol (15 ml) and heated at 80° C. for 13 hours. The reaction was concentrated in vacuo. Flash column chromatography (silica, 40 g) eluting with 2-10% MeOH/DCM afforded the desired product (200 mg, yellow oil). 1H NMR (400 MHz, CDCl3) δ 7.67-7.51 (m, 9H), 7.47-7.35 (m, 8H), 7.31-7.21 (m, 1H), 4.25 (q, J=6.8 Hz, 4H), 1.97-1.66 (m, 15H), 1.63-1.48 (m, 2H). HRMS(B) tR=1.49 min; MS m/z 222.0560

Workup

concentrationThe reaction was concentrated in vacuo
washFlash column chromatography (silica, 40 g) eluting with 2-10% MeOH/DCM

Sources & evidence

ORD record: ord-e945619f346d4e7185708695a18d7d11
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434719B2

Reaction notes

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