Cyanogen Bromide → HCID 86610628, compound

HRID 506384Notes

Reaction equation

HRID 506384 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]=[C:23]([CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=3)[C:22]([N:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:46][CH3:47])=[O:5])[CH3:2].C(=O)(O)[O-].[Na+].[N:53]#[C:54]Br>C(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:24]=[C:23]([CH2:25][C:26]3[CH:27]=[C:28]([C:36]([F:39])([F:37])[F:38])[CH:29]=[C:30]([C:32]([F:33])([F:35])[F:34])[CH:31]=3)[C:22]([N:40]3[CH2:45][CH2:44][N:43]([C:54]#[N:53])[CH2:42][CH2:41]3)=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:46][CH3:47])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 86610565HCID 86610565, compound

Product 1

HCID 86610628HCID 86610628, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2R,4S)-4-{[3,5-Bis(trifluoromethyl)benzyl]-[5-(piperazin-1-yl)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (200 mg) is dissolved in ethanol (3 ml), and thereto are added sodium bicarbonate (76.4 mg) and cyanogen bromide (35 mg). The mixture is stirred at room temperature for 13 hours, and partitioned by adding water and diethyl ether to the reaction solution. The resulting mixture is washed with saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; hexane:ethyl acetate=4:1→3:2) to give (2R,4S)-4-{[3,5-bis(trifluoromethyl)-benzyl]-[5-(4-cyanopiperazin-1-yl)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (183 mg). MS (m/z): 693 [M+H]+.

Workup

  1. custompartitioned
  2. additionby adding water and diethyl ether to the reaction solution
  3. washThe resulting mixture is washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by column chromatography (silica gel; hexane:ethyl acetate=4:1→3:2)

Sources & evidence

ORD record
ord-9e2d037c3c3d42ea8987cde4a52dda7a
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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