Water → HCID 67172219, compound

HRID 552162Notes

Reaction equation

HRID 552162 reaction equation
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:15]3[CH2:20][CH:19]4[CH:17]([CH:18]4[NH2:21])[CH2:16]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27].C(N(CC)CC)C.O>ClCCl>[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:15]3[CH2:16][CH:17]4[CH:19]([CH:18]4[NH:21][C:26](=[O:27])[C:25]4[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=4[C:23]([F:22])([F:33])[F:34])[CH2:20]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 67172284HCID 67172284, compound

Product 1

HCID 67172219HCID 67172219, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-(6-amino-3-azabicyclo[3.1.0]hex-3-yl)pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.258 g, 0.90 mmol) in dichloromethane (10 mL) was added 2-trifluoromethylbenzoyl chloride (0.2 mL, 1.00 mmol). The reaction mixture was stirred at ambient temperature for 10 minutes, followed by the addition of triethylamine (0.1 mL, 1.000 mmol). The reaction mixture was stirred at ambient temperature for another 10 minutes. Water (5.0 mL) was added to the mixture and the organic phase was separated, washed with brine, dried over MgSO4 and then concentrated in vacuo. The obtained crude product was purified by column chromatography to yield the title compound as a white powder in 15% yield (0.055 g). 1H NMR (300 MHz, CDCl3) δ 7.97 (t, J=5.5 Hz, 1H), 7.92 (d, J=9.5 Hz, 1H), 7.63-7.42 (m, 4H), 6.67 (d, J=9.4 Hz, 1H), 6.51 (s, 1H), 4.00-3.97 (m, 2H), 3.66 (d, J=10.7 Hz, 2H), 3.51-3.44 (m, 2H), 2.63 (m, 1H), 2.03 (s, 2H), 1.49-1.42 (m, 2H), 0.72-0.66 (m, 1H), 0.45-0.39 (m, 2H), 0.07-0.02 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 170.4, 168.9, 163.4, 158.1, 144.4, 135.4, 135.3, 132.0, 129.9, 128.5, 126.7, 112.5, 127.3, 48.9, 39.6, 34.5, 33.8, 24.5, 8.6, 4.2. MS (ES+) m/z 460 (M+1).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for another 10 minutes
  2. customthe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe obtained crude product
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b56be94209754f5eb8cc1198d787732a
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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