Sodium hydride → HCID 56592556, compound

HRID 1629919Notes

Reaction equation

HRID 1629919 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18]2[N:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[CH:21][N:22]=[C:23]3[NH2:28])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[H-].[Na+].Cl.[CH3:32][N:33]([CH2:35][C:36](Cl)=[O:37])[CH3:34]>CN(C=O)C>[CH3:32][N:33]([CH3:34])[CH2:35][C:36]([NH:28][C:23]1[C:24]2[C:19](=[C:18]([C:16]3[C:15]4[C:10](=[N:11][CH:12]=[CH:13][CH:14]=4)[N:9]=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])[CH:17]=3)[N:27]=[CH:26][CH:25]=2)[CH:20]=[CH:21][N:22]=1)=[O:37]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 56591765HCID 56591765, compound

Product 1

HCID 56592556HCID 56592556, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 551 mg (1.5 mmol) 5-[2-(2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-[2,6]naphthyridin-1-ylamine in 10 ml DMF was treated with 108 mg (4.50 mmol) sodium hydride and stirred for 1 h at room temperature. Then 356 mg (2.25 mmol) dimethylaminoacetyl chloride hydrochloride were added and the reaction mixture was stirred for 18 h at room temperature. The reaction mixture was partitioned between water and dichloromethane. The organic phase was dried over sodium sulfate and evaporated. The residue was chromatographed on a silica gel column with ethyl acetate/methanol as eluent yielding 2-dimethylamino-N-{5-[2-(2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-[2,6]naphthyridin-1-yl}-acetamide as brown amorphous solid; HPLC/MS (B) 1.64 min, [M+H] 453.

Workup

  1. stirringthe reaction mixture was stirred for 18 h at room temperature
  2. customThe reaction mixture was partitioned between water and dichloromethane
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on a silica gel column with ethyl acetate/methanol as eluent

Sources & evidence

ORD record
ord-de5505818f904f688f949726d5c8ddd8
Source dataset
uspto-grants-2014_07
Patent number
US08791113B2

Reaction notes

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