Trifluoroacetic acid → HCID 178427155, compound

HRID 2054007Notes

Reaction equation

HRID 2054007 reaction equation
C(OC([NH:8][C@H:9]([C:21]1[NH:25][C:24]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:23]=2[N:22]=1)[CH2:10][CH2:11][C:12]1[N:13]=[C:14]([NH:17][CH:18]([CH3:20])[CH3:19])[S:15][CH:16]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.[CH3:38][C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][C:47]=1[C:48]([N:50]1[CH2:54][CH2:53][CH2:52][CH2:51]1)=[O:49])[C:42]([OH:44])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(NC(C)C)(C)C.ClCl>CN(C)C=O>[Cl:30][C:28]1[CH:27]=[CH:26][C:24]2[NH:25][C:21]([C@@H:9]([NH:8][C:42](=[O:44])[C:41]3[CH:45]=[CH:46][C:47]([C:48]([N:50]4[CH2:54][CH2:53][CH2:52][CH2:51]4)=[O:49])=[C:39]([CH3:38])[CH:40]=3)[CH2:10][CH2:11][C:12]3[N:13]=[C:14]([NH:17][CH:18]([CH3:20])[CH3:19])[S:15][CH:16]=3)=[N:22][C:23]=2[CH:29]=1

Participants

8

Reactant 6

HCID 6422Trifluoroacetic acidHCID 7912DiisopropylamineHCID 24526ChlorineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178456845HCID 178456845, compound

Product 1

HCID 178427155HCID 178427155, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 17 from N-(tert-butoxycarbonyl)-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(2-isopropylaminothiazol-4-yl)propylamine] and trifluoroacetic acid and subsequent reaction with 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, and diisopropylamine in dimethylformamide. Yield: 45%; C29H33ClN6O2 (565.139); mass spectrum: (M+H)+=565/567 (chlorine isotope).

Sources & evidence

ORD record
ord-fd2c51dcfb0f400696df484771e823f4
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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