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Diisopropylethylamine → HCID 86710561, compound

HRID 1027168
Notes
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Reaction equation

HRID 1027168 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]1[N:13]=[N:14][C:15]([N:18]([CH3:29])[CH:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]2)=[CH:16][CH:17]=1)[C:6](O)=[O:7].[CH2:30]([NH2:33])[C:31]#[CH:32].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>CN(C=O)C.C(Cl)Cl.O.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]1[N:13]=[N:14][C:15]([N:18]([CH3:29])[CH:19]2[CH2:20][C:21]([CH3:27])([CH3:28])[NH:22][C:23]([CH3:25])([CH3:26])[CH2:24]2)=[CH:16][CH:17]=1)[C:6]([NH:33][CH2:30][C:31]#[CH:32])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 81531DiisopropylethylamineHCID 239041PropargylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867105563-Methoxy-4-(6-(methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)benzoic acid

Product 1

HCID 86710561HCID 86710561, compound
Yield 28%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a crude solution of 3-methoxy-4-(6-(methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)benzoic acid (620 mg, 1.56 mmol) in DMF (10 mL) and CH2Cl2 (10 mL) was added propargyl amine (129 mg, 2.33 mmol), DIPEA (0.82 mL, 4.67 mmol) and HATU (887 mg, 2.33 mmol). The reaction was stirred at RT overnight, then diluted with water and EtOAc. The layers were separated and the aqueous layer was concentrated and partially dissolved in MeOH. The resultant white precipitate was filtered, and the MeOH filtrate was concentrated. The filtrate was dissolved in MeOH and the resultant precipitate filtered. The filtrate was concentrated and purified via HPLC(C18 sunfire column, 20% CH3CN/H2O to 100% CH3CN, 0.1% NH4OH aq. as modifier to give 3-methoxy-4-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)-N-(prop-2-yn-1-yl)benzamide (190 mg). LCMS Rt=0.86 min (condition B); MS (M+1)=436.3. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.82 (d, J=9.6 Hz, 1H), 7.73 (d, J=8.1 Hz, 1H), 7.58 (d, J=1.5 Hz, 1H), 7.52 (dd, J=7.8, 1.5 Hz, 1H), 7.10 (d, J=9.6 Hz, 1H), 5.15-5.27 (m, 1H), 4.18 (d, J=2.3 Hz, 2H), 3.93 (s, 3H), 2.99 (s, 3H), 2.63 (t, J=2.5 Hz, 1H), 1.67 (dd, J=12.5, 3.4 Hz, 2H), 1.54 (t, J=12.5 Hz, 2H), 1.33 (s, 6H), 1.20 (s, 6H).

Workup

  1. customThe layers were separated
  2. concentrationthe aqueous layer was concentrated
  3. dissolutionpartially dissolved in MeOH
  4. filtrationThe resultant white precipitate was filtered
  5. concentrationthe MeOH filtrate was concentrated
  6. dissolutionThe filtrate was dissolved in MeOH
  7. filtrationthe resultant precipitate filtered
  8. concentrationThe filtrate was concentrated
  9. custompurified via HPLC(C18 sunfire column, 20% CH3CN/H2O to 100% CH3CN, 0.1% NH4OH aq. as modifier

Sources & evidence

ORD record
ord-aee823b565a5444584d568310d14e52c
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08729263B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes