Trifluoroacetic acid → HCID 11661994, compound

HRID 1171805Notes

Reaction equation

HRID 1171805 reaction equation
C(O[C:6]([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[N:14]=[N:15][C:16]([C:19](=[O:26])[NH:20][CH2:21][CH2:22][CH:23]3[CH2:25][CH2:24]3)=[CH:17][CH:18]=2)[CH2:9]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C1(CCNC(C2N=NC(NC3CNC3)=CC=2)=O)CC1.[F:53][C:54]([F:65])([F:64])[C:55]1[CH:63]=[CH:62][CH:61]=[CH:60][C:56]=1C(Cl)=O>ClCCl.C(N(CC)CC)C>[CH:23]1([CH2:22][CH2:21][NH:20][C:19]([C:16]2[N:15]=[N:14][C:13]([NH:12][CH:10]3[CH2:9][N:8]([C:6](=[O:7])[C:56]4[CH:60]=[CH:61][CH:62]=[CH:63][C:55]=4[C:54]([F:65])([F:64])[F:53])[CH2:11]3)=[CH:18][CH:17]=2)=[O:26])[CH2:24][CH2:25]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 672049743-[6-(2-Cyclopropylethylcarbamoyl)pyridazin-3-ylamino]azetidine-1-carboxylic acid tert-butyl esterHCID 67205412HCID 67205412, compound

Product 1

HCID 11661994HCID 11661994, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

3-[6-(2-Cyclopropylethylcarbamoyl)pyridazin-3-ylamino]azetidine-1-carboxylic acid tert-butyl ester dissolved in dichloromethane (15 mL) was treated with trifluoroacetic acid. The isolated 6-(azetidin-3-ylamino)pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.026 g, 0.100 mmol) was dissolved in dichloromethane (8 mL) and then 2-trifluoromethylbenzoyl chloride (0.022 g, 0.110 mmol) was added at ambient temperature in the presence of triethylamine (0.2 mL). The mixture was stirred at ambient temperature for 15 minutes. The solvent was evaporated and the residue was purified by column chromatography. The title compound was obtained as a white solid in 57% yield (0.0246 g). 1H NMR (300 MHz, CDCl3) (8.0 (d, J=9.0 Hz, 1H), 7.9 (br., t, 1H), 7.7 (d, J=7.0 Hz, 1H), 7.6-7.5 (m, 2H), 7.4 (d, J=7.0 Hz, 1H), 6.8 (d, J=9.0 Hz, 1H), 5.7 (br., s, 1H), 4.8 (m, 1H), 4.6 (m, 1H), 4.3 (m, 1H), 4.15 (m, 1H), 3.75 (m, 1H), 3.5 (q, J=7.0 Hz, 2H), 1.5 (q, J=7.0 Hz, 2H), 0.7 (m, 1H), 0.4 (m, 2H), 0.06 (m, 2H). MS (ES+) m/z 434 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e003c2f08a5d48f88de40937d4114d08
Source dataset
uspto-grants-2010_11
Patent number
US07829712B2

Reaction notes

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