Morpholine → HCID 16755692, compound

HRID 1968663Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[CH:27][N:26]=3)([CH3:24])[CH:21]([CH3:23])[CH3:22])=[CH:16][CH:15]=2)[O:11][N:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:24][C:20]([C:17]1[CH:16]=[CH:15][C:14]([C:12]2[O:11][N:10]=[C:9]([CH2:8][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH:13]=2)=[CH:19][CH:18]=1)([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[CH:27][N:26]=1)[CH:21]([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 50 °C

Procedure

Morpholine (17.5 μL, 0.200 mmol) was added to a stirred solution of 1e (49.0 mg, 0.100 mmol) and cesium carbonate (130 mg, 0.400 mmol) in DMF (1.00 mL) at rt. The resulting mixture was heated to 50° C. for approximately 1 h, cooled to rt, and then filtered through a short column of CELITE® eluting with EtOAc. The filtrate was concentrated in vacuo and the crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier), followed by lyophilization of the purified fractions to afford the title compound 1f. m/z (ES) 499 (MH)+.

Workup

temperaturecooled to rt
filtrationfiltered through a short column of CELITE®
washeluting with EtOAc
concentrationThe filtrate was concentrated in vacuo
customthe crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier)

Sources & evidence

ORD record: ord-6bd2635e5c2b4804a5e6c67c123c474c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426413B2

Reaction notes

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