Indole → HCID 53378472, compound

HRID 1043600Notes

Reaction equation

HRID 1043600 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.Cl[C:13]1[N:14]=[C:15]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[C:16]2[N:22]=[C:21]([CH2:23][N:24]3[CH2:29][CH2:28][CH:27]([C:30]([OH:33])([CH3:32])[CH3:31])[CH2:26][CH2:25]3)[CH:20]=[CH:19][C:17]=2[N:18]=1>CN(C=O)C>[N:3]1([C:13]2[N:14]=[C:15]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:16]3[N:22]=[C:21]([CH2:23][N:24]4[CH2:29][CH2:28][CH:27]([C:30]([OH:33])([CH3:32])[CH3:31])[CH2:26][CH2:25]4)[CH:20]=[CH:19][C:17]=3[N:18]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 798IndoleHCID 24758Sodium hydrideHCID 584049702-(1-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol

Product 1

HCID 53378472HCID 53378472, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium Hydride (60% oil dispersion, 1.5 eq) was added to a solution of indole (1.05 eq) in DMF at 0° C. and stirred until gas evolution was complete. After 30 minutes, the solution was warmed to room temperature and 2-(1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol from Example 8 (0.15 g) was added. The reaction mixture was microwaved for 15 minutes at 175° C. and run thru a Biotage isolate scx-2 cartridge. The crude was purified by reverse phase HPLC to afford 8.7 mg of 128. MS (Q1) 487.3 (M)+

Workup

  1. customThe reaction mixture was microwaved for 15 minutes at 175° C.
  2. customisolate scx-2 cartridge
  3. customThe crude was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-14e69c0a47024575bcfa23744c6e82ff
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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