Hydrochloric Acid → HCID 11520204, compound

HRID 501971Notes

Reaction equation

HRID 501971 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[C:8]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C@H:22]([CH2:37][C:38]3[CH:46]=[C:45]([CH3:47])[C:44]4[C:40](=[CH:41][N:42](COCC[Si](C)(C)C)[N:43]=4)[CH:39]=3)[C:23](=[O:36])[N:24]3[CH2:29][CH2:28][CH:27]([N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)[CH2:26][CH2:25]3)=[O:20])[CH2:15][CH2:14]1)=[CH:7]2.Cl>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[C:8]([CH:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C@H:22]([CH2:37][C:38]3[CH:39]=[C:40]4[C:44](=[C:45]([CH3:47])[CH:46]=3)[NH:43][N:42]=[CH:41]4)[C:23](=[O:36])[N:24]3[CH2:25][CH2:26][CH:27]([N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)[CH2:28][CH2:29]3)=[O:20])[CH2:17][CH2:18]1)=[CH:7]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59424297HCID 59424297, compound

Product 1

HCID 11520204HCID 11520204, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-3-(7-Methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-(8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (122 mg, 0.16 mmol) was dissolved in ethyl acetate (2 mL). Hydrochloric acid (4 N in dioxane, 3.0 mL) was added to the mixture. The reaction was stirred at room temperature for 18 h. The reaction mixture was concentrated en vacuo and purified by preparatory HPLC. Organic solvents were removed from the product fractions. The remaining aqueous solution was made basic with aqueous sodium bicarbonate and was extracted with ethyl acetate (2×). The combined organic extracts were dried (magnesium sulfate), filtered, and concentrated in vacuo. The title compound was obtained as an off-white solid in 59% yield. 1H NMR (500 MHz, DMSO-d6): δ 13.03 (s, 1H), 11.78 (s, 1H), 7.99 (s, 1H), 7.70 (m, 1H), 7.46 (m, 3H), 7.34 (dd, J=10.81, 8.09, 1H), 7.15 (m, 1H), 7.06 (s, 1H), 5.43 (m, 1H), 4.34 (m, 1H), 4.17 (m, 1H), 3.88 (m, 1H), 3.06 (m, 2H), 2.97 (m, 2H), 2.83 (m, 3H), 2.50 (m, 3H), 2.36 (m, 2H), 2.27 (m, 1H), 2.05 (m, 2H), 1.82 (d, J=12.51, 2H), 1.68 (m, 1H), 1.39 (m, 10H), 0.78-0.26 (m, 1H). Mass spec.: 643.3425 (MH)+.

Workup

  1. concentrationThe reaction mixture was concentrated en vacuo
  2. custompurified by preparatory HPLC
  3. customOrganic solvents were removed from the product fractions
  4. extractionwas extracted with ethyl acetate (2×)
  5. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45a1fe65d0994203aa875ab0cca7bdbf
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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