Trifluoroacetic acid → HCID 178463959, compound

HRID 34236Notes

Reaction equation

HRID 34236 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.[CH2:63]([N:65]([CH2:76][CH3:77])[CH2:66][CH2:67][CH2:68][CH2:69][CH:70]1[CH2:75][CH2:74][CH2:73][CH2:72][NH:71]1)[CH3:64].FC(F)(F)C(O)=O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([N:71]1[CH2:72][CH2:73][CH2:74][CH2:75][CH:70]1[CH2:69][CH2:68][CH2:67][CH2:66][N:65]([CH2:76][CH3:77])[CH2:63][CH3:64])=[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

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 15057316Diethyl-(4-piperidin-2-yl-butyl)-amineHCID 15840204Pentafluorphenol-tetramethyluronium hexafluorophosphatHCID 1784635046-chloro-4-(1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-hydroxycarbonyl-quinazoline

Product 1

HCID 178463959HCID 178463959, compound

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 diethyl-(4-piperidin-2-yl-butyl)-amine in DMSO at ambient temperature and subsequent treatment with trifluoroacetic acid.

Sources & evidence

ORD record
ord-996e5c4471d64e62b3ea35b8aa89188d
Source dataset
uspto-grants-2008_09
Patent number
US07429597B2

Reaction notes

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