HCID 57546147, compound → HCID 25159522, compound

HRID 913979Notes

Reaction equation

HRID 913979 reaction equation
[CH3:1][C:2]1[C:10]2[C:6](=[CH:7][N:8](COCC[Si](C)(C)C)[N:9]=2)[CH:5]=[C:4]([CH2:19][O:20][CH2:21][C:22]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]2)[CH:3]=1>FC(F)(F)C(O)=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:19][O:20][CH2:21][C:22]2([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]2)[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

Participants

3

Reactant 1

HCID 57546147HCID 57546147, compound

Product 1

HCID 25159522HCID 25159522, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(((7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (170 mg, 0.300 mmol) was dissolved in trifluoroacetic acid (50% in dichloromethane, 5 mL) and stirred at room temperature for 2 h. 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 2M ammonia in methanol and concentrated to give 95 mg (94%) as an amorphous solid. 1H-NMR (CDCl3, 500 MHz) δ 7.98 (s, 1H), 7.31-7.40 (m, 4H), 7.29 (s, 1H), 7.24 (m, 1H), 6.88 (s, 1H), 4.42 (s, 2H), 3.45 (s, 1H), 3.41 (s, 2H), 2.95 (m, 2H), 2.77 (m, 2H), 2.46 (s, 3H), 2.17 (m, 2H), 1.97 (m, 2H); 13C NMR (126 MHz, CDCl3) δ ppm 144.3, 140.3, 134.8, 131.5, 128.4, 127.4, 126.8, 126.1, 122.8, 120.0, 117.0, 79.2, 73.6, 50.4, 42.6, 41.9, 33.3, 17.1. Mass spec.: 336.31 (MH)+. Accurate mass spec.: m/z 336.2090 [MH]+, Δ=4.2 ppm.

Workup

  1. concentrationThe reaction was concentrated
  2. customThe cartridge was flushed with several volumes of methanol which
  3. washThe product was eluted with 2M ammonia in methanol
  4. concentrationconcentrated
  5. customto give 95 mg (94%) as an amorphous solid

Sources & evidence

ORD record
ord-e0bfdf4e70d64fa8a8cd8e82c5a24f87
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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