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Hydrochloric Acid → 6-(3,5-difluorophenyl)-2-[(3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-5-yl)methyl]pyridazin-3(2H)-one

HRID 1520064
Notes
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Reaction equation

HRID 1520064 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH2:16][C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][N:21]=[C:20]4[C:26]3[N:27]=[N:28][N:29]([C:31]4[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=4)[CH:30]=3)[N:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1.Cl>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH2:16][C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][N:21]=[C:20]4[C:26]3[N:27]=[N:28][N:29]([C:31]4[CH:39]=[CH:38][C:34]([C:35]([N:52]5[CH2:57][CH2:56][O:55][CH2:54][CH2:53]5)=[O:36])=[CH:33][CH:32]=4)[CH:30]=3)[N:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 67981025HCID 67981025, compound

Product 1

HCID 574072976-(3,5-difluorophenyl)-2-[(3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-5-yl)methyl]pyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

4-[4-(5-{[3-(3,5-difluorophenyl)-6-oxopyridazin-1(6H)-yl]methyl}-1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoic acid (218 mg; 0.22 mmol; 1.0 eq.) was added in one portion to a suspension of 1,1′-carbonyldiimidazole (97 mg; 0.60 mmol; 2.7 eq.) in DMF (20 mL). The reaction suspension was heated at 10° C. for 20 min then morpholine (100 μl; 1.15 mmol; 5.2 eq.) was added in one portion. The reaction mixture was heated at 100° C. for 16 h. It was allowed to cool to RT, poured into HCl (1N solution) and extracted with EtOAc. Combined organic phases were washed sequentially with an aqueous saturated solution of NaHCO3 and brine, dried over magnesium sulfate, filtered and concentrated. The crude was purified by preparative HPLC to give the title compound a a white solid. 1H NMR (300 MHz, DMSO-d6) δ 13.42 (s, 1H), 9.38 (s, 1H), 8.48 (s, 1H), 8.23-8.08 (m, 3H), 7.75-7.64 (m, 4H), 7.61 (d, J=8.6 Hz, 1H), 7.57-7.48 (m, 1H), 7.42-7.28 (m, 1H), 7.13 (d, J=9.8 Hz, 1H), 5.51 (s, 2H), 3.64 (s, 8H). HPLC (Condition A): Rt 3.78 min (purity 97.7%). MS (ESI−): 593.7.

Workup

  1. temperatureThe reaction mixture was heated at 100° C. for 16 h
  2. temperatureto cool to RT
  3. extractionextracted with EtOAc
  4. washCombined organic phases were washed sequentially with an aqueous saturated solution of NaHCO3 and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-cf42100ac7bc4f3b970463d8d927f3bf
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073892B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes