Diisopropylethylamine → HCID 66593605, compound

HRID 1091807Notes

Reaction equation

HRID 1091807 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[O:22][CH3:23])[C:15](=[O:24])[NH:14][N:13]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].[CH2:25]([O:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[CH3:26].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C.CN(C=O)C>[CH2:25]([O:27][CH:28]1[CH2:33][CH2:32][N:31]([C:4]([C:3]2[CH:7]=[C:8]([CH:9]=[CH:10][C:2]=2[F:1])[CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[O:22][CH3:23])[C:15](=[O:24])[NH:14][N:13]=2)=[O:5])[CH2:30][CH2:29]1)[CH3:26]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 115065194-EthoxypiperidineHCID 577918172-Fluoro-5-[(8-methoxy-4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid

Product 1

HCID 66593605HCID 66593605, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

2-fluoro-5-((8-methoxy-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid (125) (200 mg, 0.61 mmol) and 4-ethoxypiperidine (79 mg, 0.61 mmol) were added to DMF (5 mL), to this was added N-ethyl-N-isopropylpropan-2-amine (0.163 mL, 0.91 mmol) and then HBTU (347 mg, 0.91 mmol). The solvent was then removed to give a brown solid, which was dissolved in acetonitrile. A white solid precipitated, which was filtered and dried to afford the desired material as a white crystalline solid (200 mg, 74.7% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.20 (3H, t), 1.46-1.62 (1H, m), 1.63-1.82 (2H, m), 1.87-1.96 (1H, m), 3.07-3.18 (1H, m), 3.43-3.59 (5H, m), 3.77-3.82 (3H, m), 3.99-4.11 (1H, m), 4.45 (2H, s), 6.91-7.02 (1H, m), 7.11-7.28 (3H, m), 7.62-7.71 (1H, m), 8.03-8.08 (1H, m), 10.29 (1H, s); m/z (ES+) (M+H)+=440.41; HPLC RT=1.87 min.

Workup

  1. customThe solvent was then removed
  2. customto give a brown solid, which
  3. customA white solid precipitated
  4. filtrationwhich was filtered
  5. customdried

Sources & evidence

ORD record
ord-3b26822e0a634885bdece6b077339a83
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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