Taurine → HCID 53312282, compound

HRID 1967015Notes

Reaction equation

HRID 1967015 reaction equation
CO[C:3](=O)[CH2:4][NH:5][C:6](=[O:37])[C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:21]([N:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]([CH:33]3[CH2:35][CH2:34]3)[CH2:25][CH2:24]2)=[O:22])=[CH:9][C:8]=1[Cl:36].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.NCC[S:75]([OH:78])(=[O:77])=[O:76]>CN(C)C=O>[Cl:36][C:8]1[CH:9]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:21]([N:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]([CH:33]3[CH2:35][CH2:34]3)[CH2:25][CH2:24]2)=[O:22])[C:11]([Cl:13])=[CH:12][C:7]=1[C:6]([NH:5][CH2:4][CH2:3][S:75]([OH:78])(=[O:77])=[O:76])=[O:37]

Participants

6

Reactant 4

HCID 1123TaurineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 53312194{2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-acetic acid methyl ester

Product 1

HCID 53312282HCID 53312282, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.127 g (0.26 mmol) 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid (Example 29, intermediate) in 1.5 mL N,N-dimethylformamide were added 0.10 g (0.26 mmol) O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, commercially available, CAS RN 148893-10-1) and 0.13 mL (0.79 mmol) N,N-diisopropylethylamine. To the yellow solution 0.036 g (0.29 mmol) taurine (commercially available, CAS RN 107-35-7) was added and the reaction mixture stirred at room temperature for 4.5 hours. The solution was filtered using a syringe micro filter and purified on a preparative HPLC system (Phenomenex Gemini column) with a gradient of acetonitrile:water (containing 0.05% formic acid) (10:90 to 98:2) to give 0.092 g (59%) of the title compound as a brown solid. MS (ESI): m/z=591.086 [M+H]+.

Workup

  1. filtrationThe solution was filtered
  2. filtrationmicro filter
  3. custompurified on a preparative HPLC system (Phenomenex Gemini column) with a gradient of acetonitrile

Sources & evidence

ORD record
ord-fb461dfa11d944f3808c7f7c10ad19fa
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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