Diisopropylethylamine → 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-{(2R/S)-2-[(N-methyl-N-(pyridin-2-ylmethyl)-amino)-methyl]-piperidin-1-yl-carbonyl}-quinazoline

HRID 34232Notes

Reaction equation

HRID 34232 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([OH:14])=O)[N:8]=[CH:7][N:6]=[C:5]2[NH:15][CH:16]([C:18]1[NH:22][C:21]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:20]=2[N:19]=1)[CH3:17].FC1C(OC(N(C)C)=[N+](C)C)=C(F)C(F)=C(F)C=1F.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH3:63][N:64]([CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][N:74]=1)[CH2:65][CH:66]1[CH2:71][CH2:70][CH2:69][CH2:68][NH:67]1>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([N:74]1[CH2:75][CH2:76][CH2:77][CH2:78][CH:73]1[CH2:72][N:64]([CH3:63])[CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][N:67]=1)=[O:14])[N:8]=[CH:7][N:6]=[C:5]2[NH:15][CH:16]([C:18]1[NH:22][C:21]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:20]=2[N:19]=1)[CH3:17]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 15840204Pentafluorphenol-tetramethyluronium hexafluorophosphatHCID 43565105n-Methyl-n-(piperidin-2-ylmethyl)-pyridin-2-ylmethyl-amineHCID 1784635046-chloro-4-(1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-hydroxycarbonyl-quinazoline

Product 1

HCID 1784634756-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-{(2R/S)-2-[(N-methyl-N-(pyridin-2-ylmethyl)-amino)-methyl]-piperidin-1-yl-carbonyl}-quinazoline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared analogously to Example 37a from 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-hydroxycarbonyl-quinazoline, pentafluorophenyl-tetramethyluronium-hexafluorophosphate (PFTU), diisopropylethylamine and N-methyl-N-(piperidin-2-ylmethyl)-pyridin-2-ylmethyl-amine in DMSO at ambient temperature.

Sources & evidence

ORD record
ord-84b8fcb9f8774384aaefe1cbdcc08b44
Source dataset
uspto-grants-2008_09
Patent number
US07429597B2

Reaction notes

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