Sodium Hydroxide → (S)-10-[3-(2-Methoxy-ethyl)-piperazin-1-yl]-4H-3-thia-1,4,9-triaza-benzo[f]azulene-2-yl-methanol

HRID 131493Notes

Reaction equation

HRID 131493 reaction equation
C([O:3][C:4]([C:6]1[S:15][C:14]2[NH:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[N:10]=[C:9]([N:20]3[CH2:25][CH2:24][N:23](C)[C@@H:22]([CH2:27][CH2:28][O:29][CH3:30])[CH2:21]3)[C:8]=2[N:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH3:30][O:29][CH2:28][CH2:27][C@@H:22]1[NH:23][CH2:24][CH2:25][N:20]([C:9]2[C:8]3[N:7]=[C:6]([CH2:4][OH:3])[S:15][C:14]=3[NH:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[N:10]=2)[CH2:21]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 136090377HCID 136090377, compound

Product 1

HCID 135500051(S)-10-[3-(2-Methoxy-ethyl)-piperazin-1-yl]-4H-3-thia-1,4,9-triaza-benzo[f]azulene-2-yl-methanolYield 49.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine (S)-10-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-4H-3-thia-1,4,9-triaza-benzo[f]azulene-2-carboxylic acid ethyl ester (0.49 g, 1.18 mmol) in 5.0 mL THF, add 2.95 mL of LiAlH4 (1.0 M THF) dropwise at ice-water bath. After addition, remove the ice bath, stir the reaction mixture at RT. After half hour, quench the reaction by adding 1.0 N NaOH cautiously until no gas evolves. Pass the suspension through celite plug, wash repeatedly with ether, and concentrate the organic solution to a residue. Purify by flash chromatography affords 0.22 g of the title compound: mass spectrum (electrospray) (m/e): 374.0 (M+1), 372.1 (M−1); 1H NMR (400 MHz, DMSO-d6): 7.79 (s, 1H), 6.86-6.75 (m, 3H), 6.69-6.66 (m, 1H), 5.89 (br, 1H), 4.50 (d, 2H, J=4.4 Hz), 4.04-3.93 (m, 2H), 3.38-3.33 (m, 2H), 3.30 (s, 3H), 2.84-2.60 (m, 4H), 2.46-2.41 (m, 1H), 1.49 (q, 2H, J=6.6 Hz).

Workup

  1. additionAfter addition
  2. customremove the ice bath
  3. customquench
  4. customthe reaction
  5. washPass the suspension through celite plug, wash repeatedly with ether
  6. concentrationconcentrate the organic solution to a residue
  7. customPurify by flash chromatography

Sources & evidence

ORD record
ord-50a19a6be50749298fe08337a551b937
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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