Dimethylamine → HCID 178473725, compound

HRID 849427Notes

Reaction equation

HRID 849427 reaction equation
[ClH:1].Cl.Cl.[NH:4]1[CH:8]=[C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[CH:18][C:19]([C:21]4[CH:22]=N[CH:24]=[CH:25][CH:26]=4)=[CH:20][C:15]=3[CH2:14][N:13]([C:27](=[O:32])[C:28](F)(F)F)[CH:12]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:11]2)[N:6]=[CH:5]1.[CH3:40]NC>CN(C=O)C>[ClH:1].[C:27]([N:13]1[CH2:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:22]=[CH:40][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][C:16]=2[N:10]([CH2:9][C:7]2[N:6]=[CH:5][NH:4][CH:8]=2)[CH2:11][C@H:12]1[CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)(=[O:32])[CH3:28]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 178478619HCID 178478619, compound

Product 1

HCID 178473725HCID 178473725, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Compound B (7 g) and dimethylamine (2.0 M in THF, 75 mL, 150 mmol) in DMF (150 mL) was warmed to 80° C. (sealed tube) for 30 hr. The DMF was removed. The residue was passed through a short silica gel colum (5% MeOH, 0.5% NH4OH in CH2Cl2). The eluant was evaporated and the residue was purified by reverse phase preparative HPLC (gradient of aqueous methanol with 0.1% TFA) and converted to the HCl salt to provide Compound C as an off white solid (5.0 g, 60% from Compound D of Example 226) MS: (M+H)+ 544

Workup

  1. custom(sealed tube) for 30 hr
  2. customThe DMF was removed
  3. customThe eluant was evaporated
  4. customthe residue was purified by reverse phase preparative HPLC (gradient of aqueous methanol with 0.1% TFA)

Sources & evidence

ORD record
ord-bef3c84f2173493c8b17d8738e0126f7
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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