2-(Methyl(4-(trimethylstannyl)phenyl)amino)ethanol → (R)-tert-butyl 2-((7-(4-((2-hydroxyethyl)(methyl)amino)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate

HRID 57637Notes

Reaction equation

HRID 57637 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][C:9]([Sn](C)(C)C)=[CH:8][CH:7]=1)[CH2:3][CH2:4][OH:5].Cl[C:17]1[N:26]=[C:25]([NH:27][CH2:28][C@H:29]2[O:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]2)[C:24]2[C:19](=[N:20][CH:21]=[CH:22][N:23]=2)[CH:18]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:5][CH2:4][CH2:3][N:2]([CH3:1])[C:6]1[CH:11]=[CH:10][C:9]([C:17]2[N:26]=[C:25]([NH:27][CH2:28][C@H:29]3[O:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]3)[C:24]3[C:19](=[N:20][CH:21]=[CH:22][N:23]=3)[CH:18]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 710936692-(Methyl(4-(trimethylstannyl)phenyl)amino)ethanolHCID 86706988(R)-tert-butyl 2-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate

Product 1

HCID 86717398(R)-tert-butyl 2-((7-(4-((2-hydroxyethyl)(methyl)amino)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

2-(methyl(4-(trimethylstannyl)phenyl)amino)ethanol (223 mg, 0.713 mmol), (R)-tert-butyl 2-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate (246 mg, 0.648 mmol), tetrakis(triphenylphosphine)palladium (150 mg, 0.13 mmol) was mixed in toluene, reacted at 100° C. overnight. Then it was filtrated and concentrated, purified by flash chromatography (PE: EA=2:1 to 1:1) to give crude product as a reddish-brown oil. And it was used without further purification.

Workup

  1. customreacted at 100° C. overnight
  2. filtrationThen it was filtrated
  3. concentrationconcentrated
  4. custompurified by flash chromatography (PE: EA=2:1 to 1:1)
  5. customto give crude product as a reddish-brown oil
  6. customAnd it was used without further purification

Sources & evidence

ORD record
ord-8adadb20d68244eca3ec8c74e7a4b1cf
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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