Hydrochloric Acid → HCID 58529419, compound

HRID 1972765Notes

Reaction equation

HRID 1972765 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][O:35][Si](C(C)(C)C)(C)C)[CH2:29][CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>C(O)C>[NH2:26][C:24]1[C:25]2=[C:17]([C:12]3[CH:13]=[CH:14][C:15]4[C:10]([CH:11]=3)=[N:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:16]=4)[CH:18]=[C:19]([CH:27]3[CH2:28][CH2:29][N:30]([CH2:33][CH2:34][OH:35])[CH2:31][CH2:32]3)[N:20]2[N:21]=[CH:22][N:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58529383HCID 58529383, compound

Product 1

HCID 58529419HCID 58529419, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-(2-benzyl-2H-indazol-6-yl)-7-[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)piperidin-4-yl]pyrrolo[2,1-f][1,2,4]triazin-4-amine (38 mg, 0.065 mmol) in 95% aqueous ethanol (300 μL) was added concentrated hydrochloric acid (6 μL). The reaction was stirred (rt) for 48 h. The mixture was basified (pH 9) with, the addition of saturated aqueous NaHCO3 solution and was evaporated to remove volatiles. The aqueous mixture was extracted with ethyl acetate (3×20 mL) and the combined organics were washed with brine, dried (Na2SO4) and concentrated. The crude material was triturated with Et2O to afford 18 mg (61%) of the desired product as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.60 (s, 1 H), 7.94 (s, 1 H), 7.85 (d, 1 H), 7.64 (s, 1H), 7.54 (s, 1 H), 7.46-7.33 (m, 5 H), 7.20 (d, 1 H), 6.63 (s, 1 H), 5.70 (s, 2 H), 3.60-3.51 (m, 2 H), 3.18-3.08 (m, 1 H), 3.06-2.98 (m, 2 H), 2.46 (t, 2 H), 2.14 (t, 2H), 2.02 (d, 2 H), 1.82-1.68 (m, 2 H); ES-MS m/z 468.34 [M+H]+, HPLC RT (min) 0.82.

Workup

  1. customwas evaporated
  2. customto remove volatiles
  3. extractionThe aqueous mixture was extracted with ethyl acetate (3×20 mL)
  4. washthe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was triturated with Et2O

Sources & evidence

ORD record
ord-92802b35a3444f9b8f1ef1c2718ce635
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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