Water → HCID 178473236, compound

HRID 506404Notes

Reaction equation

HRID 506404 reaction equation
C([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@H:9]([C:18]2[C:23]([CH2:24][C:25]3[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=3)=[CH:22][C:21]([C:39]#[N:40])=[CH:20][N:19]=2)[CH2:8][C@@:7]1([NH2:43])[CH2:41][CH3:42])=O)C.[Cl-].[OH:45][NH3+:46].[CH2:47](N(CC)CC)[CH3:48].[OH2:54]>C(O)C.C(OCC)(=O)C>[CH2:47]([O:54][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@H:9]([C:18]2[C:23]([CH2:24][C:25]3[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=3)=[CH:22][C:21]([C:39](=[NH:40])[NH:46][OH:45])=[CH:20][N:19]=2)[CH2:8][C@@:7]1([NH2:43])[CH2:41][CH3:42])=[O:3])[CH3:48]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 21645Hydroxylamine HClHCID 86610689HCID 86610689, compound

Product 1

HCID 178473236HCID 178473236, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2R,4S)-4-{[3,5-Bis(trifluoromethyl)benzyl]-[5-cyanopyridin-2-yl]}-amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (300 mg), hydroxylammonium chloride (170 mg) and triethylamine (340 μl) are dissolved in ethanol (2 ml), and the mixture is stirred under reflux for 2 hours. The reaction solution is cooled to room temperature, and thereto are added water and ethyl acetate. The organic layer is washed with saturated brine, then dried over magnesium sulfate, and then concentrated under reduced pressure to give (2R,4S)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(N-hydroxycarbamimidoyl)pyridin-2-yl]}-amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (360 mg). MS (m/z): 641 [M+H]+.

Workup

  1. temperatureunder reflux for 2 hours
  2. washThe organic layer is washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8ffa64484054d418bcc2d9909be603b
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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