Diisopropylethylamine → 2,6-Dichloro-N-(4-chloro-3-(2-(2-(dimethylamino)ethylamino)-8-methoxy-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-isonicotinamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([OH:7])=O.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:45][C:46]1[CH:47]=[CH:48][C:49]([Cl:71])=[C:50]([C:52]2[C:67](=[O:68])[N:66]([O:69][CH3:70])[C:55]3[N:56]=[C:57]([NH:60][CH2:61][CH2:62][N:63]([CH3:65])[CH3:64])[N:58]=[CH:59][C:54]=3[CH:53]=2)[CH:51]=1>C1COCC1.C(Cl)Cl.CO.CN(C=O)C>[Cl:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([Cl:1])[N:10]=1)[C:5]([NH:45][C:46]1[CH:47]=[CH:48][C:49]([Cl:71])=[C:50]([C:52]2[C:67](=[O:68])[N:66]([O:69][CH3:70])[C:55]3[N:56]=[C:57]([NH:60][CH2:61][CH2:62][N:63]([CH3:65])[CH3:64])[N:58]=[CH:59][C:54]=3[CH:53]=2)[CH:51]=1)=[O:7]Participants
9
Reactant 4
HCID 81531Diisopropylethylamine
HCID 948302,6-Dichloroisonicotinic acid
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 584783586-(5-amino-2-chlorophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-oneProduct 1
Reagents, catalysts & solvents 4
Procedure
To a solution of 2,6-dichloroisonicotinic acid (0.37 g) in 10 ml THF was added diisopropylethylamine (0.449 ml) followed by HATU (0.733 g). After 10 min 1 ml DCM and 2 ml DMF were added. Then 6-(5-amino-2-chlorophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-one (0.5 g) was added as solution in THF (10 ml) with 1 ml DCM and 2 ml DMF. The reaction was stirred at r.t. for 1 h. The reaction mixture was diluted with 10 ml DCM, treated with 5 ml methanol and evaporated on 15 g alox (neutral).
Workup
- customevaporated on 15 g alox (neutral)
Sources & evidence
- ORD record
- ord-8a8f3af0fce64498bdf44103188dedd0
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232283B2
Reaction notes
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