Morpholine → HCID 66579017, compound

HRID 1521835Notes

Reaction equation

[CH3:1][N:2]1[C:6]2[C:7]3[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=[CH:11][C:12]=3[S:13][CH2:14][C:5]=2[C:4]([C:18]([OH:20])=O)=[N:3]1.C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.CCOC(C)=O.[NH:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1>C1COCC1>[CH3:1][N:2]1[C:6]2[C:7]3[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=[CH:11][C:12]=3[S:13][CH2:14][C:5]=2[C:4]([C:18]([N:52]2[CH2:57][CH2:56][O:55][CH2:54][CH2:53]2)=[O:20])=[N:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

To 1-methyl-8-nitro-1,4-dihydrothiochromeno[4,3-c]pyrazole-3-carboxylic acid (0.088 g, 0.30 mmol) in THF is added triethylamine (0.13 mL, 0.9 mmol, 3 Eq) followed by 50% T3P (propane phosphonic acid anhydride) in EtOAc (0.50 mL, 0.81 mmol, 2.7 Eq). The reaction mixture is cooled to 0° C. and then morpholine (0.38 mL, 0.60 mmol, 2Eq) is added and the reaction is stirred overnight at rt. Then the solvent is removed under vacuo and the residue is diluted with EtOAc. The organic layer is washed with 10% NaHCO3 followed by brine. The organic layer is dried over MgS)4and concentrated in vacuo to afford 0.084 g (77%) of the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 8.55 (d, J=2.4 Hz, 1H), 8.10 (dd, J=8.5 Hz, J=2.4 Hz, 1H), 7.76 (d, J=8.7 Hz, 1H), 4.20 (s, 3H), 4.19 (s, 2H), 3.95 (brs, 2H), 3.63 (brs, 6H). MS (ESI+): 359.0. HPLC (max plot) 96.9%; Rt 3.78 min.

Workup

customThen the solvent is removed under vacuo
additionthe residue is diluted with EtOAc
washThe organic layer is washed with 10% NaHCO3
customThe organic layer is dried over MgS)4and
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4de395e617bc45ca8fe4953eea7b2c90
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073940B2

Reaction notes

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