HCID 89996011, compound → HCID 90000938, compound

HRID 1480776Notes

Reaction equation

HRID 1480776 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]=O)=[C:10]([O:17][CH3:18])[CH:9]=2)[CH:4]=[N:3]1.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]([CH3:7])=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]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:10]([O:17][CH3:18])[CH:9]=2)[CH:4]=[N:3]1

Participants

3

Reactant 2

HCID 89996011HCID 89996011, compoundHCID 89996127HCID 89996127, compound

Product 1

HCID 90000938HCID 90000938, compoundYield 8%

Procedure

The title compound was prepared according to Example 40 using N-(4-(1,5-dimethy-1H-pyrazol-4-yl)-2-methoxyphenyl)formamide (Preparation 77) and 2-(methylsulfonyl)-N-neopentylpyrido[3,4-d]pyrimidin-8-amine (Preparation 47). The residue was purified by silica gel column chromatography eluting with 50-100% EtOAc in cyclohexane followed by a second chromatography eluting with, 50-90% EtOAc in cyclohexane. The residue was passed through a SCX-2 cartridge eluting with 100% MeOH-1M NH3 in MeOH to give the title compound (5 mg, 8%).

Workup

  1. customThe title compound was prepared
  2. customThe residue was purified by silica gel column chromatography
  3. washeluting with 50-100% EtOAc in cyclohexane
  4. washeluting with, 50-90% EtOAc in cyclohexane
  5. washeluting with 100% MeOH-1M NH3 in MeOH

Sources & evidence

ORD record
ord-8194ff39c55d48a88764d09385284ede
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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