Trifluoroacetic acid → HCID 11712014, compound

HRID 1171803Notes

Reaction equation

HRID 1171803 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[N:15]=[N:16][C:17]([C:20](=[O:27])[NH:21][CH2:22][CH2:23][CH:24]3[CH2:26][CH2:25]3)=[CH:18][CH:19]=2)[CH2:9]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C1(CCNC(C2N=NC(NC3CCNC3)=CC=2)=O)CC1.[F:55][C:56]([F:67])([F:66])[C:57]1[CH:65]=[CH:64][CH:63]=[CH:62][C:58]=1C(Cl)=O>ClCCl.C(N(CC)CC)C>[CH:24]1([CH2:23][CH2:22][NH:21][C:20]([C:17]2[N:16]=[N:15][C:14]([NH:13][CH:10]3[CH2:11][CH2:12][N:8]([C:6](=[O:7])[C:58]4[CH:62]=[CH:63][CH:64]=[CH:65][C:57]=4[C:56]([F:67])([F:66])[F:55])[CH2:9]3)=[CH:19][CH:18]=2)=[O:27])[CH2:25][CH2:26]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 67206498HCID 67206498, compoundHCID 67206647HCID 67206647, compound

Product 1

HCID 11712014HCID 11712014, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

3-[6-(2-Cyclopropylethylcarbamoyl)pyridazin-3-ylamino]pyrrolidine-1-carboxylic acid tert-butyl ester was treated with trifluoroacetic acid in dichloromethane (15 mL). The isolated 6-(pyrrolidin-3-ylamino)pyridazine-3-carboxylic acid (2-cyclopropylethyl)-amide (0.053 g, 0.19 mmol) was dissolved in dichloromethane (10 mL) and then 2-trifluoromethylbenzoyl chloride (0.040 g, 0.19 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 powder in 54% yield (0.046 g). 1H NMR (300 MHz, CDCl3) δ 8.01 (d, J=10.0 Hz, 1H), 7.7 (m, 2H), 7.6 (t, J=7.0 Hz, 1H), 7.5 (m, 2H), 6.7 (d, J=10.0 Hz, 1H), 6.2 (m, 1H), 4.8 (m, 1H), 3.9-3.60 (m, 2H), 3.5-3.4 (m, 2H), 2.4 (m, 1H), 2.2 (m, 1H), 1.4 (t, J=7.0 Hz, 2H), 0.7 (m, 1H), 0.4 (m, 2H), 0.07 (m, 2H). MS (ES+) m/z 448.1 (M+1).

Workup

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

Sources & evidence

ORD record
ord-4ba5f7ea3ab849d0a8f02dbd63754df3
Source dataset
uspto-grants-2010_11
Patent number
US07829712B2

Reaction notes

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