Lithium Hydroxide → HCID 57794582, compound

HRID 2099838Notes

Reaction equation

HRID 2099838 reaction equation
[OH-].[Li+].[O:3]=[C:4]1[C:13]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C@H:23]([CH2:28][C:29]3[CH:37]=[C:36]([CH3:38])[C:35]4[C:31](=[CH:32][N:33]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[N:34]=4)[CH:30]=3)[C:24]([O:26]C)=[O:25])=[O:21])[CH2:16][CH2:15]2)=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1>O1CCOCC1>[CH3:38][C:36]1[C:35]2[C:31](=[CH:32][N:33]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[N:34]=2)[CH:30]=[C:29]([CH2:28][C@@H:23]([O:22][C:20]([N:17]2[CH2:16][CH2:15][CH:14]([C:13]3[C:4](=[O:3])[NH:5][C:6]4[C:11]([CH:12]=3)=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:19][CH2:18]2)=[O:21])[C:24]([OH:26])=[O:25])[CH:37]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57794717HCID 57794717, compound

Product 1

HCID 57794582HCID 57794582, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Aqueous lithium hydroxide (1M, 130 mL, 0.13 mmol) was added dropwise to a stirred solution of (R)-1-methoxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxopropan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (40 mg, 0.0646 mmol) in dioxane (2 mL) at 0° C., and the mixture was stirred for 2 h. The reaction was quenched with 1N hydrochloric acid, poured into ethyl acetate (30 mL), washed with brine (10 mL), dried over magnesium sulfate and concentrated in vacuo to afford a tan foamy solid (32 mg, 82%), which was used without further purification. 1H-NMR (CDCl3, 400 MHz) δ 8.02 (s,1H), 7.60 (s,1H), 7.52-7.32 (m, 3H), 7.29-7.13 (m, 2H), 7.05 (s,1H), 5.71 (s,2H), 5.29 (dd, J=9.0, 3.8 Hz, 1H), 4.28 (br, 2H), 3.34 (br, 2H), 3.34 (dd, J=14.1, 3.9 Hz, 2H), 3.21 (dd, J=14.4, 9.2 Hz, 2H) 3.13-2.75 (m, 4H), 2.60 (s, 3H), 1.95-1.72 (m, 4H), 0.95-1.85 (m, 2H), 0.051 (s, 9H).

Workup

  1. customThe reaction was quenched with 1N hydrochloric acid
  2. additionpoured into ethyl acetate (30 mL)
  3. washwashed with brine (10 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-805bae6627764d09b64f5eecd43a9937
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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