Water → HCID 42602819, compound

HRID 2170548Notes

Reaction equation

HRID 2170548 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-cf7f344e9c4f4727a11686d344d74615
Source dataset
uspto-grants-2015_06
Patent number
US09051281B2

Reaction notes

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