Morpholine → HCID 58431155, compound

HRID 1040568Notes

Reaction equation

HRID 1040568 reaction equation
C([O:4][C:5]([C:7]1([NH:10][C:11]([C:13]2[N:17]3[C@:18]([CH3:42])([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([N:37]5[CH:41]=[N:40][CH:39]=[N:38]5)=[CH:33][CH:32]=4)[C:19](=[O:29])[N:20]([C:21]4[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=4)[C:16]3=[N:15][CH:14]=2)=[O:12])[CH2:9][CH2:8]1)=[O:6])C=C.N1CCOCC1>C1COCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:27][C:25]1[CH:26]=[C:21]([N:20]2[C:16]3=[N:15][CH:14]=[C:13]([C:11]([NH:10][C:7]4([C:5]([OH:6])=[O:4])[CH2:8][CH2:9]4)=[O:12])[N:17]3[C@:18]([CH3:42])([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([N:37]4[CH:41]=[N:40][CH:39]=[N:38]4)=[CH:33][CH:32]=3)[C:19]2=[O:29])[CH:22]=[C:23]([Cl:28])[CH:24]=1

Participants

6

Reactant 2

HCID 8083MorpholineHCID 584310531-{[(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-1,2,4-triazol-1-yl-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acid allyl ester

Product 1

HCID 58431155HCID 58431155, compoundYield 111.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-{[(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-1,2,4-triazol-1-yl-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acid allyl ester (109 mg, 0.18 mmol) and morpholine (0.157 mL, 1.80 mmol) in 1 mL of THF was added Pd(Ph3P)4 (10 mg, 0.009 mmol). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was then diluted with 30 mL of EtOAc and washed with 10 mL each of 10% HCl solution, water, and brine, dried over Na2SO4, filtered, and concentrated to afford 114 mg of 1-{[(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-1,2,4-triazol-1-yl-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acid as an orange oily solid that was carried to the next step without further purification.

Workup

  1. washwashed with 10 mL each of 10% HCl solution, water, and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5b979f9f9ff94eb8a799997d16dd8a3e
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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