Toluene → HCID 18548816, compound

HRID 1266844Notes

Reaction equation

HRID 1266844 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH2:18][C:19](=[O:33])[NH:20][C:21]4[CH:27]=[C:26]([N:28]5[CH:32]=[CH:31][CH:30]=[CH:29]5)[CH:25]=[CH:24][C:22]=4[N:23]=3)[CH:12]=2)[S:9][CH:10]=1)=O)C.COCCO[AlH2-]OCCOC.[Na+].C1(C)C=CC=CC=1>C1COCC1>[OH:3][CH2:4][C:6]1[N:7]=[C:8]([C:11]2[CH:12]=[C:13]([C:17]3[CH2:18][C:19](=[O:33])[NH:20][C:21]4[CH:27]=[C:26]([N:28]5[CH:29]=[CH:30][CH:31]=[CH:32]5)[CH:25]=[CH:24][C:22]=4[N:23]=3)[CH:14]=[CH:15][CH:16]=2)[S:9][CH:10]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 16684438Red-AlHCID 69779722HCID 69779722, compound

Product 1

HCID 18548816HCID 18548816, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 2-[3-(4-oxo-7-pyrrol-1-yl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-phenyl]-thiazole-4-carboxylic acid ethyl ester (Example 19) (0.34 g, 0.75 mmol) in THF (35 mL) was added at −20° C. over 40 min in 3 portions a 3.5 M solution of sodium dihydrido-bis(2-methoxyethoxy)aluminate in toluene (0.94 mL, 3.3 mmol). Stirring was continued at −20° C. for 20 min. and the reaction mixture was then poured into ice-cold 10% aqueous acetic acid. The product was extracted with EtOAc and the organic layer was washed successively with H2O, sat. Na2CO3-solution and brine, dried over Na2SO4 and evaporated in vacuum. The residue was triturated with methanol to give the title compound (0.28 g) as light-yellow solid.

Workup

  1. extractionThe product was extracted with EtOAc
  2. washthe organic layer was washed successively with H2O, sat. Na2CO3-solution and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuum
  5. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-5a52749075f14944b0cd9458bfa151e2
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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