Aluminium lithium hydride → HCID 68458113, compound

HRID 2197780Notes

Reaction equation

HRID 2197780 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([NH:18][C:19]2[C:28]3[C:23](=[N:24][C:25]([CH3:29])=[CH:26][CH:27]=3)[N:22]=[CH:21][CH:20]=2)[CH:6]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:29][C:25]1[N:24]=[C:23]2[C:28]([C:19]([NH:18][C:7]3[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[CH:9][C:8]=3[S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:20][CH:21]=[N:22]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68460795HCID 68460795, compound

Product 1

HCID 68458113HCID 68458113, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 53c (2.30 g, 5.54 mmol) in 60 mL of THF was reacted with the LiAlH4 (420 mg, 11.0 mmol) for 18 h followed quenching with dilute HCl. Adjusted to pH 10 with NH4OH. Extracted with CH2Cl2, dried over MgSO4 filtered and concentrated under vacuum giving the crude title compound which was purified by HPLC with TFA providing the trifluoroacetic acid salt (325 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.76 (s, 3H) 3.99 (br. s, 1H) 4.58 (s, 2H) 6.31 (d, J=7.35 Hz, 1H) 7.25 (s, 5H) 7.40 (m, 2H) 7.46 (s, 1H) 7.78 (d, J=8.82 Hz, 1H) 8.42 (d, J=6.99 Hz, 1H) 8.95 (d, J=8.46 Hz, 1H) 11.06 (br. s., 1H) 14.44 (br. s., 1H); MS (ESI+) m/z 374 (M+H)+.

Workup

  1. customfollowed quenching with dilute HCl
  2. extractionExtracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-09ba94e9b03345468a1a92a0c84bd2c1
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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