HCID 89996011, compound → HCID 89996108, compound

HRID 1480777Notes

Reaction equation

HRID 1480777 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]=O)=[C:9]([O:16][CH3:17])[CH:8]=2)=[CH:5][N:4]=[C:3]1[CH3:18].CS(C1[N:24]=[CH:25][C:26]2[CH:32]=[CH:31][N:30]=[C:29]([NH:33][CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:27]=2[N:28]=1)(=O)=O>>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:24]=[CH:25][C:26]4[CH:32]=[CH:31][N:30]=[C:29]([NH:33][CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:27]=4[N:28]=3)=[C:9]([O:16][CH3:17])[CH:8]=2)=[CH:5][N:4]=[C:3]1[CH3:18]

Participants

3

Reactant 2

HCID 89996011HCID 89996011, compoundHCID 89996058HCID 89996058, compound

Product 1

HCID 89996108HCID 89996108, compoundYield 21%

Procedure

The title compound was prepared according to Example 40 using N-(4-(1,2-dimethyl-1H-imidazol-5-yl)-2-methoxyphenyl)formamide (Preparation 55) and 2-(methylsulfonyl)-N-neopentylpyrido[3,4-d]pyrimidin-8-amine (Preparation 47). The residue was purified by silica gel column chromatography eluting with 0-10% MeOH in EtOAc. The residue was purified by passage through a SCX-2 cartridge eluting with 100% MeOH-1M NH3 in MeOH. The residue was diluted with DCM (30 mL) and washed with 0.1M HCl (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was further purified by SCX-2 cartridge eluting with 100% MeOH-1M NH3 in MeOH followed by silica gel column chromatography eluting with 0-7% MeOH in EtOAc to give the title compound (5.5 mg, 21%).

Workup

  1. customThe title compound was prepared
  2. customThe residue was purified by silica gel column chromatography
  3. washeluting with 0-10% MeOH in EtOAc
  4. customThe residue was purified by passage through a SCX-2 cartridge
  5. washeluting with 100% MeOH-1M NH3 in MeOH
  6. additionThe residue was diluted with DCM (30 mL)
  7. washwashed with 0.1M HCl (30 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was further purified by SCX-2 cartridge
  11. washeluting with 100% MeOH-1M NH3 in MeOH
  12. washeluting with 0-7% MeOH in EtOAc

Sources & evidence

ORD record
ord-ed21f72d962b41939bdd520e5008b774
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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