Lithium Hydroxide → HCID 57899118, compound

HRID 76074

Reaction equation

HRID 76074 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[N:13][C:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.C[O:58][C:59](=[O:65])[C@H:60]([CH:62]([CH3:64])[CH3:63])[NH2:61].[Li+].[OH-]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[N:13][C:12]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([NH:61][CH:60]([CH:62]([CH3:64])[CH3:63])[C:59]([OH:65])=[O:58])=[O:21])=[CH:22][CH:23]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 3939Lithium HydroxideHCID 81531DiisopropylethylamineHCID 94285Valine methyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 666157634-[6-(3-Chloro-phenylamino)-pyridazin-3-yl]-benzoic acid

Product 1

HCID 57899118HCID 57899118, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[6-(3-Chloro-phenylamino)-pyridazin-3-yl]-benzoic acid (0.10 g, 0.31 mmol, 1.0 equiv) in 2 Ml DMF was added HATU (0.23 g, 0.62 mmol, 2.0 equiv) and N,N-diisopropylethylamine (0.27 Ml, 1.5 mmol, 5.0 equiv). Valine methyl ester (0.062 g, 0.37 mmol, 1.0 equiv) was added as a solid, and the homogeneous solution was allowed to stir at room temperature overnight. To the solution was then added 1 Ml 10% aqueous LiOH, and the mixture was then heated to 55° C. The reactions were then filtered and the purified by reverse-phase HPLC to afford the title compound: 1H NMR (400 MHz, MeOD) δ 0.96 (dd, J=9.35, 6.82 Hz, 6H) 2.21 (dq, J=12.13, 6.82 Hz, 1H) 4.41 (d, J=5.05 Hz, 1H) 6.91 (ddd, J=1.26 Hz, 2.02, 1.01 Hz, 1H) 7-21 (t, J=8.08 Hz, 1H) 7.17 (d, J=9.35 Hz, 1H) 7.48 (dd, J=9.22, 1.14 Hz, 1H) 7.88-8.02 (m, 7H); (M+H)+425.1.

Workup

  1. temperaturethe mixture was then heated to 55° C
  2. filtrationThe reactions were then filtered
  3. customthe purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-715d6600209c4b43a21af7fddffe5c13
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Linked notes

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