Trifluoroacetic acid → HCID 68358961, compound

HRID 1408982Notes

Reaction equation

HRID 1408982 reaction equation
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:12]=[C:6]2[C:5]=1[NH:19][C@H:20]1[CH2:24][CH2:23][C@@:22]([CH2:26][NH:27]C(=O)OC(C)(C)C)([CH3:25])[C:21]1([CH3:36])[CH3:35])(=[O:3])[NH2:2].FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[NH2:27][CH2:26][C@@:22]1([CH3:25])[CH2:23][CH2:24][C@H:20]([NH:19][C:5]2[C:6]3[N:7]([CH:10]=[C:11]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:12]=3)[N:8]=[CH:9][C:4]=2[C:1]([NH2:2])=[O:3])[C:21]1([CH3:36])[CH3:35]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68358692HCID 68358692, compound

Product 1

HCID 68358961HCID 68358961, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (((1S,3S)-3-((3-carbamoyl-6-phenylpyrrolo[1,2-b]pyridazin-4-yl)amino)-1,2,2-trimethylcyclopentyl)methyl)carbamate (236 mg, 0.480 mmol) in dichloromethane (3910 μl) at 0° C. was added trifluoroacetic acid (452 μl, 5.87 mmol. The reaction mixture was allowed to warm to room temperature and stirring was continued for 1 hr. The reaction mixture was concentrated under reduced pressure, yielding a yellow oil. The oil was diluted with ethyl acetate (50 ml) and washed successively with saturated sodium bicarbonate, water, and saturated sodium chloride. The ethyl acetate extract was dried with sodium sulfate, filtered, and concentrated under reduce pressure, yielding 4-(((1S,3S)-3-(aminomethyl)-2,2,3-trimethylcyclopentyl)amino)-6-phenylpyrrolo[1,2-b]pyridazine-3-carboxamide (182 mg, 0.465 mmol, 97% yield) as a tan solid. ESI-MS m/z 392.3 ([M+H]+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customyielding a yellow oil
  3. washwashed successively with saturated sodium bicarbonate, water, and saturated sodium chloride
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-63dbb6a8adf94ebcb881a9653147479f
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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