Morpholine → HCID 21906815, compound

HRID 1005799Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH:21]([CH3:23])[CH3:22])=[C:10]([C:24]([F:27])([F:26])[F:25])[CH:9]=2)[N:5]=[CH:4][N:3]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:7]=2)=[CH:9][C:10]=1[C:24]([F:27])([F:26])[F:25])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of compound 47 (0.015 g, 0.0367 mmol) in DMF (1.0 mL) was added morpholine followed by potassium carbonate (0.015 g, 0.109 mmol). The reaction mixture was heated at 80° C. for 16 hours. The solid was removed through filtration, and the filtrate was directly purified by preparative HPLC, to give a yellow solid, 43 (0.012 g, 72%). 1H-NMR (CDCl3, 400 MHz) δ 1.19 (d, J=6.8 Hz, 6H), 3.51 (heptet, J=6.8 Hz, 1H), 3.69 (t, J=4.9 Hz, 4H), 3.81 (t, J=4.9 Hz, 4H), 6.80 (s, 1H), 6.90 (d, J=8.5 Hz, 1H), 7.20-7.24 (m, 1H), 7.43 (s, 1H), 7.44 (s, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.87 (d, J=8.2 Hz, 1H), 8.26 (s, 1H), 8.67(s, 1H). MS (APCI) m/z 460 (M+H)+.

Workup

customThe solid was removed through filtration
customthe filtrate was directly purified by preparative HPLC

Sources & evidence

ORD record: ord-5693dde5656f4a7abd3ab7de8d4f53b1
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787542B2

Reaction notes

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