Trifluoroacetic acid → HCID 66931544, compound

HRID 1929520Notes

Reaction equation

HRID 1929520 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([F:50])=[C:17]([C@:19]2([CH3:49])[CH2:24][O:23][CH2:22][C:21]([NH:25]C(C3C=CC(OC)=CC=3)(C3C=CC(OC)=CC=3)C3C=CC=CC=3)=[N:20]2)[CH:18]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C.FC(F)(F)C(O)=O>ClCCl>[ClH:1].[NH2:25][C:21]1[CH2:22][O:23][CH2:24][C@:19]([C:17]2[CH:18]=[C:13]([NH:12][C:8]([C:5]3[C:4]([F:11])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)=[O:10])[CH:14]=[CH:15][C:16]=2[F:50])([CH3:49])[N:20]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117690705-Chloro-3-fluoropyridine-2-carboxylic acidHCID 66931535HCID 66931535, compound

Product 1

HCID 66931544HCID 66931544, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to example 22 a) the reaction of 5-chloro-3-fluoro-pyridine-2-carboxylic acid and Building block J, [(R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-[bis-(4-methoxy-phenyl)-phenyl-methyl]-amine, using O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate as the condensating agent in presence of Huenig's base, followed by the cleavage of the [bis-(4-methoxy-phenyl)-phenyl-methyl]-(DMTr) amino protecting group with trifluoroacetic acid in dichloromethane yielded the title compound (yield: 24% of theory). Mass (calculated) C17H15ClF2N4O2.ClH [417.241]; (found) [M+H]+=381.

Sources & evidence

ORD record
ord-012c391d86a6476197aa1b17e74357b2
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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