Diisopropylethylamine → HCID 178472219, compound

HRID 2096110

Reaction equation

HRID 2096110 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[O:4][N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:43]([O:45][C:46](=[O:68])[C@@:47]([OH:67])([CH3:66])[CH2:48][N:49]([CH2:51][C:52]1[CH:57]=[CH:56][C:55]([C:58]2[CH:63]=[C:62]([Cl:64])[CH:61]=[CH:60][C:59]=2[F:65])=[CH:54][CH:53]=1)[NH2:50])[CH3:44]>CN(C=O)C>[CH2:43]([O:45][C:46](=[O:68])[C@@:47]([OH:67])([CH3:66])[CH2:48][N:49]([CH2:51][C:52]1[CH:53]=[CH:54][C:55]([C:58]2[CH:63]=[C:62]([Cl:64])[CH:61]=[CH:60][C:59]=2[F:65])=[CH:56][CH:57]=1)[NH:50][C:7]([C:5]1[O:4][N:3]=[C:2]([OH:1])[CH:6]=1)=[O:9])[CH3:44]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68180853(R)-3-[N-(5'-chloro-2'-fluorobiphenyl-4-ylmethyl)-hydrazino]-2-hydroxy-2-methyl-propionic acid ethyl esterHCID 178524642HCID 178524642, compound

Product 1

HCID 178472219HCID 178472219, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxyisoxazole-5-carboxylic acid (132 mg, 1.0 mmol) and HATU (389 mg, 1.0 mmol) were combined in DMF (3.7 mL), and the resulting mixture was stirred for 10 minutes at room temperature. DIPEA (343 μL, 2.0 mmol) and (R)-3-[N-(5′-chloro-2′-fluorobiphenyl-4-ylmethyl)-hydrazino]-2-hydroxy-2-methyl-propionic acid ethyl ester (300 mg, 0.8 mmol) were added and the resulting mixture was stirred for 30 minutes. LC/MS showed desired product. The mixture was the evaporated under reduced pressure to yield the title compound (210 mg, 100% purity). MS m/z [M+H]+ calc'd for C23H23ClFN3O6, 492.13; found 492.2.

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes

Sources & evidence

ORD record
ord-10901c0acc04453699426c653d48bf47
Source dataset
uspto-grants-2013_05
Patent number
US08449890B2

Linked notes

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