HCID 57545923, compound → HCID 25159650, compound

HRID 913983Notes

Reaction equation

HRID 913983 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[C:16]([CH2:18][O:19][CH2:20][C:21]3([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)[C:15]3[C:11](=[CH:12][N:13]([CH3:40])[N:14]=3)[CH:10]=2)=[CH:5][CH:4]=1)#[N:2]>FC(F)(F)C(O)=O>[CH3:40][N:13]1[CH:12]=[C:11]2[C:15]([C:16]([CH2:18][O:19][CH2:20][C:21]3([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]3)=[CH:17][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)=[CH:10]2)=[N:14]1

Participants

3

Reactant 1

HCID 57545923HCID 57545923, compound

Product 1

HCID 25159650HCID 25159650, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(((5-(4-cyanophenyl)-2-methyl-2H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (29 mg, 0.054 mmol) was dissolved in trifluoroacetic acid (25% in dichloromethane, 4 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 20 mg (85%) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 7.94 (s, 1H), 7.71 (m, 3H), 7.61 (m, 2H), 7.41 (m, 2H), 7.30 (m, 3H), 7.18 (m, 1H), 4.89 (s, 2H), 4.21 (s, 3H), 3.60 (s, 2H), 2.90 (m, 2H), 2.75 (m, 2H), 2.19 (m, 2H), 1.95 (m, 2H), 1.92 (bs, 1H); 13C-NMR (CDCl3, 126 MHz) δ 147.0, 146.4, 144.6, 132.9, 132.6, 128.8, 128.3, 127.8, 127.4, 126.0, 124.8, 122.5, 122.3, 119.3, 117.5, 110.3, 80.2, 68.9, 42.8, 42.0, 40.7, 33.7. Mass spec.: 437.17 (MH)+. Accurate mass spec.: m/z 437.2339 [MH]+, Δ=0.5 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 20 mg (85%) as a colorless film

Sources & evidence

ORD record
ord-cbaeb55e52fe4304a76f63e5714265e5
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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