HCID 68875256, compound → HCID 25159652, compound

HRID 913985Notes

Reaction equation

HRID 913985 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH3:33])=[CH:8][C:9]=2[CH2:11][O:12][CH2:13][C:14]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[CH2:4][NH:3]1>FC(F)(F)C(O)=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH3:33])=[CH:8][C:9]=2[CH2:11][O:12][CH2:13][C:14]2([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)[CH:4]=[N:3]1

Participants

3

Reactant 1

HCID 68875256HCID 68875256, compound

Product 1

HCID 25159652HCID 25159652, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(((1,5-dimethyl-2H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (24 mg, 0.053 mmol) was dissolved in trifluoroacetic acid (25% in dichloromethane, 1.5 mL) and stirred at room temperature for 45 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 to give 18.8 mg (quant.) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 7.81 (s, 1H), 7.39 (s, 1H), 7.26 (m, 4H), 7.18 (m, 1H), 6.94 (s, 1H), 4.63 (s, 2H), 3.89 (s, 3H), 3.42 (s, 2H), 2.80 (m, 2H), 2.69 (m, 2H), 2.39 (s, 3H), 2.08 (m, 2H), 1.81 (m, 2H), 1.50-2.00 (bs, 1H); 13C-NMR (CDCl3, 126 MHz) δ 144.3, 137.4, 132.0, 130.8, 129.3, 128.3, 127.2, 126.1, 126.0, 120.5, 119.9, 79.0, 71.2, 42.7, 41.7, 38.0, 33.7, 21.1. Mass spec.: 350.05 (MH)+. Accurate mass spec.: m/z 350.2222 [MH]+, Δ=3.0 ppm.

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. customto give 18.8 mg (quant.) as a colorless film

Sources & evidence

ORD record
ord-b2bea69cef5242bc8360a0c35b41cf93
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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