Aluminium lithium hydride → HCID 58203708, compound

HRID 1849352Notes

Reaction equation

HRID 1849352 reaction equation
C(O[C:6]([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]3[O:25][CH2:24][CH2:23][C:22]4[CH:21]=[C:20]([C:26]5[N:27]([C:31]6[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=6[F:38])[N:28]=[CH:29][N:30]=5)[S:19][C:18]=4[C:17]=3[N:39]=2)[CH2:9]1)=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:38][C:32]1[CH:33]=[C:34]([F:37])[CH:35]=[CH:36][C:31]=1[N:27]1[C:26]([C:20]2[S:19][C:18]3[C:17]4[N:39]=[C:13]([NH:12][CH:10]5[CH2:9][N:8]([CH3:6])[CH2:11]5)[CH:14]=[CH:15][C:16]=4[O:25][CH2:24][CH2:23][C:22]=3[CH:21]=2)=[N:30][CH:29]=[N:28]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58204134HCID 58204134, compound

Product 1

HCID 58203708HCID 58203708, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{2-[2-(2,4-Difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulen-9-ylamino}-azetidine-1-carboxylic acid tert-butyl ester (300 mg, 0.54 mmol) was dissolved in THF (20 mL), and LiAlH4 was added in the solution. The reaction mixture was stirred at room temperature for 2 hr, filtered to gather the solution, washed by DCM (10 mL), and separated by TLC (DCM/EtOAc=10:1) to give 433 (128.3 mg, yield: 51%). 1H NMR (DMSO-d6, 400 MHz): δ8.36 (s, 1H), 8.28-7.95 (m, 2H), 7.75-7.56 (m, 1H), 7.54 (s, 1H), 6.98-6.83 (m, 1H), 6.73-6.55 (m, 1H), 4.10 (m, 6H), 3.55 (s, 1H), 3.48 (s, 1H), 3.02 (t, J=8.0 Hz, 2H). LC-MS (ESI): m/z=467 [M+H]+

Workup

  1. filtrationfiltered
  2. washwashed by DCM (10 mL)
  3. customseparated by TLC (DCM/EtOAc=10:1)

Sources & evidence

ORD record
ord-3cefb45aa02646b8809111c3ba2abd09
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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