Morpholine → HCID 23585078, compound

HRID 1640183Notes

Reaction equation

HRID 1640183 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:7][C:8]([C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:26]=[C:25]3[C:20]([CH:21]=[CH:22][C:23]([C:27]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:31]=4)=[O:28])=[CH:24]3)=[CH:19][CH:18]=2)[CH:13]=[CH:12][N:11]=1)=S>CCOC(C)=O.[Cl-].[Na+].O>[C:36]([C:32]1[CH:31]=[C:30]([NH:29][C:27]([C:23]2[CH:22]=[CH:21][C:20]3[C:25](=[CH:26][C:17]([O:16][C:14]4[CH:13]=[CH:12][N:11]=[C:10]([C:8](=[NH:7])[N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)[CH:15]=4)=[CH:18][CH:19]=3)[CH:24]=2)=[O:28])[CH:35]=[CH:34][CH:33]=1)([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 58902362HCID 58902362, compound

Product 1

HCID 23585078HCID 23585078, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Morpholine (2.00 mL, 22.9 mmol) and 7-{[2-(aminocarbonothioyl)pyridin-4-yl]-oxy}-N-(3-tert-butylphenyl)-2-naphthamide (0.155 g, 0. 34 mmol) were combined. The reaction mixture was allowed to stir at rt overnight in a sealed vial. And then heated at 60° C. for 6 h. The reaction mixture was diluted with EtOAc and poured into brine. The aqueous and organic solutions were separated and the aqueous solution was further extracted with EtOAc. The organic solutions were combined, dried over Na2SO4, and loaded onto a silica gel column. The product was collected from the column, concentrated, and redissolved in MeOH. To this solution was added 1M HCl in Et2O. The solution was concentrated to give N-(3-tert-butylphenyl)-7-({2-[imino(morpholin-4-yl)methyl]pyridin-4-yl}oxy)-2-naphthamide I-99 (21 mg). 1H NMR (400 MHz, CD3OD; 2*HCl salt) δ: 8.48 (d, 1H), 8.47 (s, 1H), 7.99-8.12 (m, 3H), 7.81 (dd, 2H), 7.58 (dd, 1H), 7.46 (dd, 1H), 7.31 (dd, 1H), 7.22 (ddd, 1H), 7.14 (d, 1H), 7.08 (d, 1H), 3.69 (dd, 4H), 3.31-3.33 (m, 4H), and 1.35 (s, 9H). LCMS: (FA) ES30 509.3, ES− 507.3.

Workup

  1. temperatureAnd then heated at 60° C. for 6 h
  2. customThe aqueous and organic solutions were separated
  3. extractionthe aqueous solution was further extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customThe product was collected from the column
  6. concentrationconcentrated
  7. dissolutionredissolved in MeOH
  8. additionTo this solution was added 1M HCl in Et2O
  9. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-81d1d0f2fbbc48438070748d5a221752
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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