Trifluoroacetic acid methylene chloride → HCID 178506217, compound

HRID 914001Notes

Reaction equation

HRID 914001 reaction equation
[CH:1]1([C:4]2[N:5](COCC[Si](C)(C)C)[N:6]=[C:7]3[C:12]=2[CH:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=[C:8]3[CH2:17][O:18][CH2:19][C:20]2([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C(Cl)Cl>>[CH:1]1([C:4]2[C:12]3[C:7](=[C:8]([CH2:17][O:18][CH2:19][C:20]4([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]4)[CH:9]=[C:10]([C:13]([F:15])([F:14])[F:16])[CH:11]=3)[NH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 57546172HCID 57546172, compound

Product 1

HCID 178506217HCID 178506217, compound

Procedure

tert-Butyl 4-(((3-cyclopropyl-5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (18 mg, 0.03 mmol) was treated with a trifluoroacetic acid/methylene chloride mixture (1:1, 2 mL) for 4 h. The solvent was removed in vacuo and the resulting crude mixture passed through a strong cation exchange column. After washing the column with several volumes of methanol, the product was eluted by washing the column with 2 M ammonia in methanol. The solvent was evaporated to afford 9 mg (77%) as a clear oil. 1H-NMR (CDCl3, 500 MHz) δ 7.92 (s, 1H), 7.31-7.45 (m, 5H), 7.22-7.33 (m, 1H), 4.67 (s, 2H), 3.52 (s, 2H), 2.95-2.99 (m, 2H), 2.76-2.81 (m, 2H), 2.15-2.24 (m, 3H), 1.89-1.95 (m, 2H), 1.04-1.02 (m, 4H). Mass spec.: 430.16 (MH)+. Accurate mass spec.: m/z 430.2097 [MH]+, Δ=2.1 ppm.

Workup

  1. customThe solvent was removed in vacuo
  2. washAfter washing the column with several volumes of methanol
  3. washthe product was eluted
  4. washby washing the column with 2 M ammonia in methanol
  5. customThe solvent was evaporated
  6. customto afford 9 mg (77%) as a clear oil

Sources & evidence

ORD record
ord-764a042b996645ec98d4f444f7ed6a01
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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