Diisopropylethylamine → (2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-7,7-dimethylazepan-2-one

HRID 74962Notes

Reaction equation

HRID 74962 reaction equation
N[CH:2]1CCN(C)[C:3]1=[O:8].Cl[C:10]1C=C2C(B3OC(C)(C)C(C)(C)O3)=CN(S(C3C=CC(C)=CC=3)(=O)=O)C2=NC=1.[Cl:38][C:39]1[CH:40]=[C:41]2[C:47]([C:48]3[N:53]=[C:52](S(C)=O)[C:51]([F:57])=[CH:50][N:49]=3)=[CH:46][N:45](S(C3C=CC(C)=CC=3)(=O)=O)[C:42]2=[N:43][CH:44]=1.[CH:68]1[CH:73]=N[C:71]2N(O)[N:75]=[N:76][C:70]=2[CH:69]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C.C1COCC1.CC(N(C)C)=O>[Cl:38][C:39]1[CH:40]=[C:41]2[C:47]([C:48]3[N:53]=[C:52]([NH:75][N:76]4[C:70]([CH3:10])([CH3:71])[CH2:69][CH2:68][CH2:73][CH2:2][C:3]4=[O:8])[C:51]([F:57])=[CH:50][N:49]=3)=[CH:46][NH:45][C:42]2=[N:43][CH:44]=1

Participants

9

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 457911333-Amino-1-methylpyrrolidin-2-oneHCID 575977475-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 672853215-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine

Product 1

HCID 131731864(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-7,7-dimethylazepan-2-one

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

3-amino-1-methylpyrrolidin-2-one, DMA, 140° C. microwave; (b) LiOH, THF, microwave, 120° C. (c) EDCI, HOAt, iPr2NEt, DCM-DMF (2:1).

Sources & evidence

ORD record
ord-63f9388e3d49420ca475eac23a69f6c9
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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