Water → HCID 42602819, compound

HRID 450524Notes

Reaction equation

HRID 450524 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[CH:20]=[C:21]([CH:26]=[C:27]([C:29]([NH:31][CH3:32])=[O:30])[CH:28]=3)[C:22](OC)=[O:23])=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[CH:28]=[C:27]([C:29]([NH:31][CH3:32])=[O:30])[CH:26]=[C:21]([CH2:22][OH:23])[CH:20]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59583424HCID 59583424, compound2×

Product 1

HCID 42602819HCID 42602819, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 3-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]-5-[(methylamino)carbonyl]benzoate (intermediate 31) (0.206 g, 0.43 mmol) in THF (5 mL), was added a 1M solution of LiAlH4 in THF (0.65 mL, 1.5 eq.). The reaction was stirred at RT for one night. Water was added and the compound was extracted with AcOEt, dried over sodium sulfate and concentrated in vacuo. After trituration from hot methanol, filtration and dry, the title compound was obtained as a white solid (0.03 g, 15.8%). HRMS calculated for C20H19Cl2N5O3 (M+H)+448.0943, found: 448.0910, Rt: 2.66 min. MP: 223-225° C.

Workup

  1. extractionthe compound was extracted with AcOEt
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. filtrationAfter trituration from hot methanol, filtration
  5. customdry

Sources & evidence

ORD record
ord-7a9c826683d6497bb46e059a2016e42b
Source dataset
uspto-grants-2013_07
Patent number
US08486977B2

Reaction notes

Loading…