HCID 89996011, compound → HCID 73386778, compound

HRID 1480772Notes

Reaction equation

HRID 1480772 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH:9][CH:10]=O)=[CH:7][CH:6]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:4]=1.CS(C1[N:23]=[CH:24][C:25]2[CH:31]=[CH:30][N:29]=[C:28]([NH:32][CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:26]=2[N:27]=1)(=O)=O>>[CH3:1][O:2][C:3]1[C:8]([NH:9][C:10]2[N:23]=[CH:24][C:25]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:26]=3[N:27]=2)=[CH:7][CH:6]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:4]=1

Participants

3

Reactant 2

HCID 89996011HCID 89996011, compoundHCID 89996059HCID 89996059, compound

Product 1

HCID 73386778HCID 73386778, compoundYield 14%

Procedure

The title compound was prepared according to Example 40 using N-(2-methoxy-6-morpholinopyridin-3-yl)formamide (Preparation 71) and 2-(methylsulfonyl)-N-neopentylpyrido[3,4-d]pyrimidin-8-amine (Preparation 47). The residue was purified by silica gel column chromatography eluting with 0-5% MeOH EtOAc followed by a second chromatography eluting with 50-100% EtOAc in cyclohexane. The residue was dissolved in EtOAc and washed with HCl (0.5 M, 10 mL), dried (MgSO4) and concentrated in vacuo. The residue was further purified by passage through a SCX-2 cartridge eluting with 100% MeOH—1 M NH3 in MeOH, to afford the title compound (10 mg, 14%).

Workup

  1. customThe title compound was prepared
  2. customThe residue was purified by silica gel column chromatography
  3. washeluting with 0-5% MeOH EtOAc
  4. washeluting with 50-100% EtOAc in cyclohexane
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with HCl (0.5 M, 10 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was further purified by passage through a SCX-2 cartridge
  10. washeluting with 100% MeOH—1 M NH3 in MeOH

Sources & evidence

ORD record
ord-9861b79e3a3644aaa821dfd2c9ec8bb9
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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