Nitrogen → HCID 58148041, compound

HRID 1043846Notes

Reaction equation

HRID 1043846 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:18]=[C:19](Br)[C:12]2=[N:11][C:10]=1[C:27]1[S:28][C:29]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[CH:30][N:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:40]([N:43]1[CH2:47][CH2:46][NH:45][C:44]1=[O:48])([CH3:42])[CH3:41].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+].N#N>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:18]=[C:19]([N:45]3[CH2:46][CH2:47][N:43]([CH:40]([CH3:42])[CH3:41])[C:44]3=[O:48])[C:12]2=[N:11][C:10]=1[C:27]1[S:28][C:29]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[CH:30][N:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 947NitrogenHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 217190151-(Propan-2-yl)imidazolidin-2-oneHCID 58148075HCID 58148075, compound

Product 1

HCID 58148041HCID 58148041, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Benzyloxy-9-bromo-2-[5-(4-fluoro-benzyl)-thiazol-2-yl]-7-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-one (product of example 218, 110 mg, 0.18 mmol), 1-isopropyl-imidazolidin-2-one (30 mg, 0.22 mmol), Pd2(dba)3 (15 mg, 0.02 mmol), Xantphos (15 mg, 0.2 mmol), Cs2CO3 (58.5 mg, 0.18 mmol) were mixed in anhydrous dioxane (5 ml). The mixture was heated at 90° C. under the atmosphere of N2 for 4 h, after which water was added and then extracted with ethyl acetate. The extracts were combined, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography to give the desired product (95 mg, yield 81%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5b593c4381ea45a0bc1279bc804bc81d
Source dataset
uspto-grants-2013_10
Patent number
US08563562B2

Reaction notes

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