Water → HCID 86610606, compound

HRID 506375Notes

Reaction equation

HRID 506375 reaction equation
[CH2:1]([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]([NH:18][C:19]2[N:24]=[CH:23][C:22]([Br:25])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH3:26])=[O:5])[CH3:2].[H-].[Na+].[F:29][C:30]([F:44])([F:43])[C:31]1[CH:32]=[C:33]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:34]Br.O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([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]([NH:18][C:19]2[N:20]=[C:21]([CH2:34][C:33]3[CH:36]=[C:37]([C:39]([F:41])([F:42])[F:40])[CH:38]=[C:31]([C:30]([F:29])([F:43])[F:44])[CH:32]=3)[C:22]([Br:25])=[CH:23][N:24]=2)[CH2:8][C@H:7]1[CH3:26])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 68714832HCID 68714832, compound

Product 1

HCID 86610606HCID 86610606, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2R*,4S*)-4-(5-Bromopyrimidin-2-yl)amino-6-methoxy-2-methyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (5.9 g) is dissolved in N,N-dimethylformamide (60 ml), then thereto is added sodium hydride(62.7%, 697 mg) at room temperature, and the mixture is stirred for 10 minutes. After adding 3,5-bis(trifluoromethyl)benzyl bromide (3.85 ml), the mixture is stirred at room temperature for 2 hours. Water and ethyl acetate is added to the reaction solution, the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is crystallized from diisopropyl ether and hexane to give (2R*,4S*)-4-{[3,5-bis(trifluoromethyl)benzyl]-(5-bromopyrimidin-2-yl)}amino-6-methoxy-2-methyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (6.1 g). MS (m/z): 648/650 [M+H]+

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is crystallized from diisopropyl ether and hexane

Sources & evidence

ORD record
ord-c914c0ce8d544284a1aaa25e437e9d8c
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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