HCID 57546178, compound → HCID 57546093, compound

HRID 913857Notes

Reaction equation

HRID 913857 reaction equation
[CH3:1][N:2]([CH3:36])[C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH:12]([O:14][CH2:15][C:16]3([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[CH3:13])[CH:11]=1)[NH:8][N:7]=[CH:6]2>FC(F)(F)C(O)=O>[F:35][C:32]1[CH:33]=[CH:34][C:29]([C:16]2([CH2:15][O:14][CH:12]([C:10]3[CH:11]=[C:3]([N:2]([CH3:1])[CH3:36])[CH:4]=[C:5]4[C:9]=3[NH:8][N:7]=[CH:6]4)[CH3:13])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:30][CH:31]=1

Participants

3

Reactant 1

HCID 57546178HCID 57546178, compound

Product 1

HCID 57546093HCID 57546093, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(±)-tert-Butyl 4-((1-(5-(dimethylamino)-1H-indazol-7-yl)ethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (138 mg, 0.278 mmol) was dissolved in trifluoroacetic acid (20% in dichloromethane, 7.5 mL) and stirred at room temperature for 30 min. The reaction was concentrated and loaded onto a strong cation exchange cartridge in methanol. The cartridge was flushed with several volumes of methanol which were discarded. The product was eluted with 2 M ammonia in methanol and concentrated to give 101 mg (92%). LC/MS (HPLC method 3): tR=1.133 min, 397.42(MH)+.

Workup

  1. concentrationThe reaction was concentrated
  2. customThe cartridge was flushed with several volumes of methanol which
  3. washThe product was eluted with 2 M ammonia in methanol
  4. concentrationconcentrated
  5. customto give 101 mg (92%)

Sources & evidence

ORD record
ord-ebfd258753904ef2ac93f159c154a7b8
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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