Morpholine → HCID 178496439, compound

HRID 1247394Notes

Reaction equation

HRID 1247394 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([CH2:7][NH:8][C:9]([CH:11]([O:23][CH3:24])[C:12]2[C:13]([F:22])=[C:14]([CH:18]=[CH:19][C:20]=2[F:21])[C:15](O)=[O:16])=[O:10])=[CH:5][CH:4]=1)#[N:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.Cl.[NH2:46][OH:47]>CN(C=O)C.CCN(CC)CC>[F:22][C:13]1[C:14]([C:15]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[O:16])=[CH:18][CH:19]=[C:20]([F:21])[C:12]=1[CH:11]([O:23][CH3:24])[C:9]([NH:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:1](=[NH:2])[NH:46][OH:47])=[CH:26][CH:25]=1)=[O:10]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 69292797HCID 69292797, compound

Product 1

HCID 178496439HCID 178496439, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution under Ar of (RS)-3-[(4-cyano-benzylcarbamoyl)-methoxy-methyl]-2,4-difluoro-benzoic acid (150 mg) in DMF (2 ml) was added 1,1′-carbonyldiimidazole (74 mg). The reaction mixture was stirred 15 min at rt before addition of morpholine. After stirring 2 h at rt hydroxylamine hydrochloride (289 mg) and Et3N (0.3 ml) were added. The reaction mixture was stirred 20 h at rt, then it was poured on H2O (20 ml) and extracted with AcOEt (2×20 ml). The organic layers were washed with brine and dried (Na2SO4) and the solvent was evaporated. CC (AcOEt/MeOH 99:1 to 9:1) yielded 111 mg (58%) of (RS)-2-[2,6-difluoro-3-(morpholine-4-carbonyl)-phenyl]-N-[4-(N-hydroxycarbamimidoyl)-benzyl]-2-methoxy-acetamide. White solid. MS 463.5 ([M+H]+).

Workup

  1. additionwere added
  2. additionit was poured on H2O (20 ml)
  3. extractionextracted with AcOEt (2×20 ml)
  4. washThe organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5d6d421d061342d4873ae1836a535763
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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