Morpholine → N-cyclopropylsulfonyl-13-methyl-17-(2-morpholin-4-ylpyrimidin-4-yl)oxy-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxamide

HRID 1429158Notes

Reaction equation

HRID 1429158 reaction equation
[CH:1]1([S:4]([NH:7][C:8]([C:10]2([NH:15][C:16]([CH:18]3[CH2:22][CH:21]([O:23][C:24]4[CH:29]=[CH:28][N:27]=[C:26](Cl)[N:25]=4)[CH2:20][CH:19]3[C:31]([N:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40])[CH3:34])=[O:32])=[O:17])[CH2:12][CH:11]2C=C)=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>C1COCC1.ClCCCl>[CH3:34][N:33]1[C:31](=[O:32])[CH:19]2[CH:18]([CH2:22][CH:21]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([N:41]4[CH2:46][CH2:45][O:44][CH2:43][CH2:42]4)[N:25]=3)[CH2:20]2)[C:16](=[O:17])[NH:15][C:10]2([C:8]([NH:7][S:4]([CH:1]3[CH2:3][CH2:2]3)(=[O:6])=[O:5])=[O:9])[CH:11]([CH2:12]2)[CH:40]=[CH:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 72253694N-(1-Cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-2-(hex-5-enyl-methyl-amino-carbonyl)-4-(2-chloropyrimidin-4-yloxy)-cyclopentane-carboxamide

Product 1

HCID 75277256N-cyclopropylsulfonyl-13-methyl-17-(2-morpholin-4-ylpyrimidin-4-yl)oxy-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxamide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

Compound 10f (31 mg, 0.052 mmol) and morpholine (0.1 ml) in THF was left at ambient temperature for 20 hrs, volatiles were stripped of and the residue was dissolved in DCE (15 ml) to which Hoyeda-Grubbs II catalyst (7 mg) was added. The mixture was heated in a microwave oven at 150° C. for 10 min under an atmosphere of nitrogen, then concentrated to dryness and purified by column chromatography on silica gel eluted with DCM-MeOH 2% followed by prep. HPLC-MS-UV to give pure title compound, (4.7 mg), (M+H)+616.2.

Workup

  1. additionwas added
  2. concentrationconcentrated to dryness
  3. custompurified by column chromatography on silica gel
  4. washeluted with DCM-MeOH 2%

Sources & evidence

ORD record
ord-260d242a672143c88b65a3f3221c55c0
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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