Trifluoroacetic acid → HCID 71604413, compound

HRID 1396472Notes

Reaction equation

HRID 1396472 reaction equation
[C:1]([C:4]1[N:9]=[N:8][C:7]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:17]C(=O)OC(C)(C)C)=[CH:6][C:5]=1[NH:25][C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH2:33][CH2:34][CH3:35])[N:27]=1)(=[O:3])[NH2:2].FC(F)(F)C(O)=O>ClCCl>[NH2:17][C@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[NH:10][C:7]1[N:8]=[N:9][C:4]([C:1]([NH2:2])=[O:3])=[C:5]([NH:25][C:26]2[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH2:33][CH2:34][CH3:35])[N:27]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86689802tert-butyl (1S,2R)-2-(6-carbamoyl-5-(4-methyl-6-propylpyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate

Product 1

HCID 71604413HCID 71604413, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (1S,2R)-2-(6-carbamoyl-5-(4-methyl-6-propylpyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (91 mg, 188 μmol) in dichloromethane (2.9 mL) was added trifluoroacetic acid (429 mg, 290 μL, 3.76 mmol) and the mixture stirred at room temperature for 16 h. The mixture was concentrated in vacuo then diluted with NH4OH and dichloromethane. The mixture was washed with water, then the organic phase was concentrated in vacuo and purified by chromatography (silica, 3 to 15% methanol in dichloromethane) to give 6-((1R,2S)-2-aminocyclohexylamino)-4-(4-methyl-6-propylpyridin-2-ylamino)pyridazine-3-carboxamide (46 mg, 120 μmol, 64%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.59 (s, 1H), 8.34 (s, 1H), 8.08 (s, 1H), 7.63 (s, 1H), 6.80 (d, J=7.2 Hz, 1H), 6.70 (s, 1H), 6.60 (s, 1H), 3.88 (s, 1H), 3.25 (s, 1H), 2.67 (t, J=7.4 Hz, 1H), 2.26 (s, 3H), 1.71 (m, 2H), 1.54-1.71 (m, 6H), 1.35 (s, 2H), 0.93 (t, J=7.2 Hz, 3H); MS (EI/CI) m/z: 384.1 [M+H].

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthen diluted with NH4OH and dichloromethane
  3. washThe mixture was washed with water
  4. concentrationthe organic phase was concentrated in vacuo
  5. custompurified by chromatography (silica, 3 to 15% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f12779666ec3437293a6de8e89b67afa
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

Loading…