Diisopropylethylamine → (R)-4-(2,4-Dimethoxybenzylamino)-3-(4-(8-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino)benzonitrile

HRID 605863Notes

Reaction equation

HRID 605863 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][C@H:7]2[NH2:12].C(N(CC)C(C)C)(C)C.[CH3:22][O:23][C:24]1[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:25]=1[CH2:26][NH:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=1[NH:36][C:37]1[N:42]=[C:41](SC#N)[C:40]([N+:46]([O-:48])=[O:47])=[CH:39][N:38]=1>CS(C)=O.C1COCC1.CCOC(C)=O>[CH3:22][O:23][C:24]1[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:25]=1[CH2:26][NH:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=1[NH:36][C:37]1[N:42]=[C:41]([NH:12][C@H:7]2[C:6]3[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=3)[O:10][CH2:9][CH2:8]2)[C:40]([N+:46]([O-:48])=[O:47])=[CH:39][N:38]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 46911919(R)-8-fluorochroman-4-amineHCID 566052112-(5-Cyano-2-{[(2,4-dimethoxyphenyl)methyl]amino}anilino)-5-nitropyrimidin-4-yl thiocyanate

Product 1

HCID 59704995(R)-4-(2,4-Dimethoxybenzylamino)-3-(4-(8-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino)benzonitrileYield 96.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-8-Fluorochroman-4-amine (HCl salt, 0.45 g, 2.2 mmol) was dissolved in 1 mL DMSO with 1.7 mL N,N-diisopropylethyl amine (9.7 mmol) in 40 mL anhydrous THF. To this solution was added 0.93 g (2.0 mmol) 4-(2,4-dimethoxybenzylamino)-3-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)benzonitrile. The slightly cloudy mixture was stirred at room temperature for 16 hrs under Argon balloon till HPLC showed the completion of reaction. The mixture became clear then. The reaction mixture was diluted with EtOAc, washed with brine twice, and then dried over Na2SO4. Solvents were removed under vacuum to give 1.1 g dark red solid as the crude product.

Workup

  1. customthe completion of reaction
  2. washwashed with brine twice
  3. dry with materialdried over Na2SO4
  4. customSolvents were removed under vacuum

Sources & evidence

ORD record
ord-7ca6aab196f74a56b6331b66d36c3393
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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