Trifluoroacetic acid → HCID 178463483, compound

HRID 34176

Reaction equation

HRID 34176 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12](O)=[O:13])[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.C(OC([CH:70]([NH2:77])[CH2:71][C@@H:72]1[CH2:76][CH2:75][CH2:74][NH:73]1)=O)(C)(C)C.FC(F)(F)C(O)=O>CS(C)=O>[NH2:77][CH2:70][CH2:71][C@@H:72]1[CH2:76][CH2:75][CH2:74][N:73]1[C:12]([C:11]1[CH:10]=[C:9]2[C:4]([C:5]([NH:15][CH:16]([C:18]3[NH:22][C:21]4[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:20]=4[N:19]=3)[CH3:17])=[N:6][CH:7]=[N:8]2)=[CH:3][C:2]=1[Cl:1])=[O:13]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 15840204Pentafluorphenol-tetramethyluronium hexafluorophosphatHCID 131727083(2s)-2-(2-Tert.-butyloxycarbonyl-aminoethyl)-pyrrolidineHCID 1784635046-chloro-4-(1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-hydroxycarbonyl-quinazoline

Product 1

HCID 178463483HCID 178463483, 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 (2S)-2-(2-tert.-butyloxycarbonyl-aminoethyl)-pyrrolidine in DMSO at ambient temperature and subsequent treatment with trifluoroacetic acid.

Sources & evidence

ORD record
ord-cf7ab2643357470fbd3089a45fcdbfe6
Source dataset
uspto-grants-2008_09
Patent number
US07429597B2

Linked notes

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