Diisopropylethylamine → (R)-2-((tert-butoxycarbonyl)amino)-4-(4-((4-((1-(4-chlorophenyl)cyclopropyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)butanoic acid

HRID 1407051Notes

Reaction equation

HRID 1407051 reaction equation
C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2([NH:44][C:45]3[N:50]=[C:49]([O:51][CH2:52][C:53]([F:56])([F:55])[F:54])[N:48]=[C:47]([NH:57][C:58]4[CH:66]=[CH:65][C:61]([C:62](O)=[O:63])=[CH:60][CH:59]=4)[N:46]=3)[CH2:43][CH2:42]2)=[CH:37][CH:36]=1.[NH2:67][CH2:68][CH2:69][C@@H:70]([NH:74][C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])[C:71]([OH:73])=[O:72]>CN(C=O)C>[C:78]([O:77][C:75]([NH:74][C@H:70]([CH2:69][CH2:68][NH:67][C:62](=[O:63])[C:61]1[CH:60]=[CH:59][C:58]([NH:57][C:47]2[N:46]=[C:45]([NH:44][C:41]3([C:38]4[CH:39]=[CH:40][C:35]([Cl:34])=[CH:36][CH:37]=4)[CH2:43][CH2:42]3)[N:50]=[C:49]([O:51][CH2:52][C:53]([F:56])([F:54])[F:55])[N:48]=2)=[CH:66][CH:65]=1)[C:71]([OH:73])=[O:72])=[O:76])([CH3:81])([CH3:80])[CH3:79]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 7021116Boc-D-2,4-diaminobutyric acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 667654164-(4-(1-(4-Chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid

Product 1

HCID 86691690(R)-2-((tert-butoxycarbonyl)amino)-4-(4-((4-((1-(4-chlorophenyl)cyclopropyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)butanoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Di-iso-propylethylamine (0.054 g) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.079 g) were added into a solution of 4-((4-((1-(4-chlorophenyl)cyclopropyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoic acid (0.1 g) and (R)-4-amino-2-((tert-butoxycarbonyl)amino)butanoic acid (0.045 g) in DMF (1 mL). The reaction was stirred at room temperature for 16 hours and (R)-2-((tert-butoxycarbonyl)amino)-4-(4-((4-((1-(4-chlorophenyl)cyclopropyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)butanoic acid was isolated by using preparative HPLC system.

Sources & evidence

ORD record
ord-20523567d6624bb08448ccd6843f2749
Source dataset
uspto-grants-2014_12
Patent number
US08916702B2

Reaction notes

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