Diisopropylethylamine → HCID 16059439, compound

HRID 1710631Notes

Reaction equation

HRID 1710631 reaction equation
Cl.Cl.[F:3][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1.[Cl:17][C:18]1[CH:31]=[CH:30][C:21]2[N:22]([CH2:26][C:27](O)=[O:28])[C:23](=[O:25])[O:24][C:20]=2[CH:19]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN1C(=O)CCC1>[Cl:17][C:18]1[CH:31]=[CH:30][C:21]2[N:22]([CH2:26][C:27]([N:12]3[CH2:13][CH2:14][N:9]([CH2:8][C:7]4[CH:15]=[CH:16][C:4]([F:3])=[CH:5][CH:6]=4)[CH2:10][CH2:11]3)=[O:28])[C:23](=[O:25])[O:24][C:20]=2[CH:19]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 776366(6-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 126798621-[(4-Fluorophenyl)methyl]piperazine--hydrogen chloride (1/2)

Product 1

HCID 16059439HCID 16059439, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 4 mL vial was added 1-(4-fluoro-benzyl)-piperazine dihydrochloride (13) (51 mg, 0.22 mmol, 1.0 equiv), (6-chloro-2-oxo-benzooxazol-3-yl)-acetic acid (50 mg, 0.22 mmol, 1.00 equiv), DIEA (153 μL, 0.88 mmol, 4.0 equiv), HATU (100 mg, 0.26 mmol, 1.20 equiv) and 1.5 mL of NMP. A stir bar was placed in the vial and the vial was then capped. The resultant mixture stirred at room temperature overnight. The crude product was purified by reversed phase HPLC (acetonitrile —H2O with 0.1% TFA as the eluent) to yield 6-chloro-3-{2-[4-(4-fluoro-benzyl)-piperazin-1-yl]-2-oxo-ethyl}-3H-benzooxazol-2-one (14): HPLC retention time, 1.05 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.) using 1 ml/min flow rate, a 2.5 minute gradient of 20% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expected, 403.8, found, 404.5.

Workup

  1. customA stir bar was placed
  2. customin the vial and the vial was then capped
  3. customThe crude product was purified by reversed phase HPLC (acetonitrile —H2O with 0.1% TFA as the eluent)

Sources & evidence

ORD record
ord-1809a0b09c5d4c228a42a60f86ff1d3d
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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