Morpholine → HCID 57510343, compound

HRID 624224Notes

Reaction equation

HRID 624224 reaction equation
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([N:17]3[CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18]3)=[O:16])=[CH:10][CH:9]=2)[N:4]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>CN(C=O)C.CO>[N:26]1([CH2:2][C:3]2[O:7][N:6]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([NH:14][C:15]([N:17]4[CH2:25][C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[CH2:18]4)=[O:16])=[CH:10][CH:9]=3)[N:4]=2)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 68749928HCID 68749928, compound

Product 1

HCID 57510343HCID 57510343, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a 20 mL vial was added N-(4-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)phenyl)isoindoline-2-carboxamide (50 mg, 0.141 mmol) and morpholine (36.8 mg, 0.423 mmol) in DMF (470 μl). The mixture was heated to 50° C. for 30 minutes, cooled, and diluted with 2 mL methanol. Chromatography provided the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.69 (s, 1H), 7.92 (d, J=8.8 Hz, 2H), 7.80 (d, J=8.9 Hz, 2H), 7.35 (ddd, J=8.8, 3.9, 2.4 Hz, 4H), 4.80 (s, 4H), 3.95 (s, 2H), 3.68-3.48 (m, 4H), 2.62-2.51 (m, 5H); MS (ESI(+)) m/e 406 (M+H)+.

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-585640eddf0446a390ce3c9d7c02bdfe
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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