HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Diisopropylethylamine → 4-(4-Cyclohexanecarbonyl-piperazine-1-carbonyl)-pyridin-2-ylmethyl-2H-phthalazin-1-one

HRID 2217316
Notes
Print preview

Reaction equation

HRID 2217316 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12]C2C=C(C=CN=2)C(O)=O)=[N:4][NH:3]1.[CH:22]1([C:28]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.CN(C(O[N:44]1N=N[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.CC[O:71]C(C)=O.CO>>[CH:22]1([C:28]([N:30]2[CH2:31][CH2:32][N:33]([C:12]([C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:2](=[O:1])[N:3]([CH2:50][C:49]4[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=4)[N:4]=3)=[O:71])[CH2:34][CH2:35]2)=[O:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 34375021-(Cyclohexylcarbonyl)piperazineHCID 21584119Ethylacetate methanolHCID 597677412-(4-Oxo-3,4-dihydro-phthalazin-1-ylmethyl)-isonicotinic acid

Product 1

HCID 131726981
4-(4-Cyclohexanecarbonyl-piperazine-1-carbonyl)-pyridin-2-ylmethyl-2H-phthalazin-1-one

Procedure

To a stirred solution of 2-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-isonicotinic acid (iva) (0.25 g, 0.89 mol) in diemthylacetamide (2 mL) was added cyclohexyl-piperazin-1-yl-methanone (0.20 g, 1.0 mmol) followed by HBTU (0.38 g, 1.0 mmol) and diisopropyl ethyl amine (0.35 mL, 20.0 mmol) and stirred. The reaction mixture was then concentrated in vacuo and resulting oil subjected to flash chromatography eluent 9:1 EtOAc/MeOH. (rf of 0.3) The titled compound was isolated as a white solid. Single peak in LC-MS analysis, (0.18 g, 56%); m/z (LC-MS, ESP), RT=4.07 mins, (M+H)=460; 1H NMR (300 MHz) 12.57 (1H, S-NH), 8.56 (1H, d, J 5.1 Hz), 8.26 (1H, dd, J 1.5, 8.1 Hz), 7.95-7.80 (3H, m), 7.38 (1H, S), 7.25 (1H, d, J 5.7 Hz), 4.51 (2H, S), 3.56-3.17 (8H, m), 2.58 (1H, m), 1.71-1.61 (5H, m), 1.38-1.22 (5H, m).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customresulting oil

Sources & evidence

ORD record
ord-4ff2aa88688a40b190589f80c97e9b7e
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07407957B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes