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Tetrahydrofuran → 1-[3-(6-tert-Butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-[4-(morpholine-4-carbonyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amide

HRID 1025586
Notes
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Reaction equation

HRID 1025586 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[C:17]([CH2:44][OH:45])=[C:18]([N:22]3[CH:26]=[C:25]([C:27]#[N:28])[C:24]([NH:29][C:30]4[CH:35]=[CH:34][C:33]([C:36]([N:38]5[CH2:43][CH2:42][O:41][CH2:40][CH2:39]5)=[O:37])=[CH:32][CH:31]=4)=[N:23]3)[CH:19]=[CH:20][CH:21]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C1C[O:49]CC1>O>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[C:17]([CH2:44][OH:45])=[C:18]([N:22]3[CH:26]=[C:25]([C:27]([NH2:28])=[O:49])[C:24]([NH:29][C:30]4[CH:35]=[CH:34][C:33]([C:36]([N:38]5[CH2:39][CH2:40][O:41][CH2:42][CH2:43]5)=[O:37])=[CH:32][CH:31]=4)=[N:23]3)[CH:19]=[CH:20][CH:21]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 710083501-[3-(6-tert-Butyl-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl]-3-[4-(morpholine-4-carbonyl)phenylamino]-1H-pyrazole-4-carbonitrile

Product 1

HCID 710082871-[3-(6-tert-Butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-[4-(morpholine-4-carbonyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amideYield 76.6%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

1-[3-(6-tert-Butyl-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl]-3-[4-(morpholine-4-carbonyl)phenylamino]-1H-pyrazole-4-carbonitrile (52 mg, 0.0861 mmol) was dissolved in 4 mL of THF and 0.4 mL of water. Then dihydrogen tris(dimethylphosphinito)hydroplatinate (CAS#173416-05-2, 3 mg, 8% eq) was added. The mixture was refluxed for 1 hr. TLC indicated complete consumption of the starting material. LC/MS indicated the clean product formed with the correct MW. The mixture was evaporated to dryness and then dissolved in dichloromethane, dried over sodium sulfate and filtered. After the evaporation of solvents, the residue was purified through flash column chromatography (24 g silica gel, methanol in dichloromethane, 0% to 5% in 16 minutes) to give 1-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-[4-(morpholine-4-carbonyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amide as a white solid (41 mg, 76.6% yield). LC/MS clacd for C34H35N7O5 (m/e) 621.27, obsd 622.1 (M+H, ES+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.41 (s, 9H) 3.41-3.71 (m, 8H), 4.37 (br. s., 2H), 4.74 (br. s., 1H), 7.36 (d, J=6.3 Hz, 3H), 7.49-7.71 (m, 5H), 7.80 (br. s., 1H), 8.04 (d, J=9.1 Hz, 2H), 8.25 (d, J=6.6 Hz, 1H), 8.56 (br. s., 2H), 9.44 (br. s., 1H).

Workup

  1. temperatureThe mixture was refluxed for 1 hr
  2. customconsumption of the starting material
  3. customformed with the correct MW
  4. customThe mixture was evaporated to dryness
  5. dissolutiondissolved in dichloromethane
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customAfter the evaporation of solvents
  9. customthe residue was purified through flash column chromatography (24 g silica gel, methanol in dichloromethane, 0% to 5% in 16 minutes)

Sources & evidence

ORD record
ord-8057a0d1728841c3b9fea247bf0e5280
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08729078B2

Reaction notes

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