Diisopropylethylamine → (S)-Ethyl 4-((4-methoxybenzyl)amino)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxylate

HRID 1052388Notes

Reaction equation

HRID 1052388 reaction equation
[NH2:1][C@H:2]([C:4]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8](=[O:16])[C:7]2=[C:17]([CH3:20])[CH:18]=[CH:19][N:6]2[N:5]=1)[CH3:3].Cl[C:22]1[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:26]([NH:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)[N:25]=[CH:24][N:23]=1.C(N(CC)C(C)C)(C)C>C(O)C>[CH3:42][O:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][NH:33][C:26]2[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:22]([NH:1][C@H:2]([C:4]3[N:9]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:8](=[O:16])[C:7]4=[C:17]([CH3:20])[CH:18]=[CH:19][N:6]4[N:5]=3)[CH3:3])[N:23]=[CH:24][N:25]=2)=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 90102580(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneHCID 90102730Ethyl 4-chloro-6-((4-methoxybenzyl)amino)pyrimidine-5-carboxylate

Product 1

HCID 131736128(S)-Ethyl 4-((4-methoxybenzyl)amino)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one was treated with ethyl 4-chloro-6-((4-methoxybenzyl)amino)pyrimidine-5-carboxylate (6 mg, 0.02 mmol), N,N-diisopropylethylamine (16 μl, 0.09 mmol) and ethanol as a solvent according to the method described in Example 17. The solvent was concentrated and the solid was suspended in ethanol and filtered. The white solid obtained was washed with ether and dried in the oven to give 281 mg (82% yield) of the title compound as a white solid.

Workup

  1. concentrationThe solvent was concentrated
  2. filtrationfiltered
  3. customThe white solid obtained
  4. washwas washed with ether
  5. customdried in the oven

Sources & evidence

ORD record
ord-903de1719e954e66900df58f2f9a1774
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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