Diisopropylethylamine → HCID 118497067, compound

HRID 522081Notes

Reaction equation

HRID 522081 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([F:25])[C:22]([C:26]2[C:31]([F:32])=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]([OH:20])=O)[CH:8]=1)=[O:5].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1C2C(=NC=CC=2)N(OC(N(C)C)=[N+](C)C)N=1.[NH2:66][CH2:67][C@@H:68]([OH:70])[CH3:69]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:24]=[C:23]([F:25])[C:22]([C:26]2[C:31]([F:32])=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]([NH:66][CH2:67][C@@H:68]([OH:70])[CH3:69])=[O:20])[CH:8]=1)=[O:5]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118497091HCID 118497091, compound

Product 1

HCID 118497067HCID 118497067, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(2-chloro-4-fluoro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid (Example 110, 100 mg, 0.22 mmol) in DMF (3 mL) was added DIPEA (0.23 mL, 1.32 mmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (92 mg, 0.26 mmol). The reaction was stirred at room temperature for 10 minutes before the addition of (S)-1-aminopropan-2-ol (20 mg, 0.22 mmol) and the reaction was continued stirring for 18 hours. The reaction was diluted with EtOAc (50 mL) and extracted with water (3×5 mL) and brine (25 mL). The organic layer was collected, dried over anhydrous Na2SO4 before concentration in vacuo. The residue was purified using reverse phase column chromatography eluting with 0-80% MeCN in water to afford the title compound (18 mg, 16%).

Workup

  1. extractionextracted with water (3×5 mL) and brine (25 mL)
  2. customThe organic layer was collected
  3. dry with materialdried over anhydrous Na2SO4 before concentration in vacuo
  4. customThe residue was purified
  5. washeluting with 0-80% MeCN in water

Sources & evidence

ORD record
ord-de99183cfe004bb4a201f208885d839f
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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