HCID 57546148, compound → HCID 25159523, compound

HRID 913982Notes

Reaction equation

HRID 913982 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[C:16]([CH2:18][O:19][CH2:20][C:21]4([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)[CH:17]=2)[N:14]([CH3:40])[N:13]=[CH:12]3)=[CH:5][CH:4]=1)#[N:2]>FC(F)(F)C(O)=O>[CH3:40][N:14]1[C:15]2[C:11](=[CH:10][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)=[CH:17][C:16]=2[CH2:18][O:19][CH2:20][C:21]2([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)[CH:12]=[N:13]1

Participants

3

Reactant 1

HCID 57546148HCID 57546148, compound

Product 1

HCID 25159523HCID 25159523, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(((5-(4-cyanophenyl)-1-methyl-1H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (63 mg, 0.117 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 47.3 mg (92%) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 7.98 (s, 1H), 7.85 (d, J=1.5 Hz, 1H), 7.70 (m, 4H), 7.35 (d, J=1.5 Hz, 1H), 7.25 (m, 4H), 7.17 (m, 1H), 4.72 (s, 2H), 3.93 (s, 3H), 3.48 (s, 2H), 2.83 (m, 2H), 2.69 (m, 2H), 2.11 (m, 2H), 1.81 (m, 2H), 1.78 (bs, 1H); 13C-NMR (CDCl3, 126 MHz) δ 145.7, 144.2, 138.5, 133.5, 132.7, 131.4, 128.4, 127.9, 127.8, 127.2, 126.24, 126.20, 121.2, 120.2, 119.1, 110.5, 79.5, 71.1, 42.7, 41.7, 38.2, 33.7. Mass spec.: 437.19 (MH)+. Accurate mass spec.: m/z 437.2354 [MH]+, Δ=2.9 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 47.3 mg (92%) as a colorless film

Sources & evidence

ORD record
ord-e6703c35a0894f8dac9179d1845b040d
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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