Hydrochloric Acid → HCID 42603213, compound

HRID 450516Notes

Reaction equation

HRID 450516 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:28]=[CH:27][C:22]([C:23](OC)=[O:24])=[CH:21][C:20]=3[O:29][CH3:30])=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CC(C[AlH]CC(C)C)C.[NH4+].[Cl-].Cl>C1COCC1.O>[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]=[CH:27][C:22]([CH2:23][OH:24])=[CH:21][C:20]=3[O:29][CH3:30])=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 42603011HCID 42603011, compound

Product 1

HCID 42603213HCID 42603213, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]-3-(methyloxy)benzoate (Example 17) (0.1 g, 0.2 mmol) in THF was added a 1M solution of DIBAL-H in THF (800 μL, 4 eq) and the reaction was stirred to room temperature for 2 hours. Solid NH4Cl was added followed by water and a 1N HCl solution. The aqueous phase was extracted with ether and AcOEt, dried over sodium sulphate and evaporated. After recrystallisation from acetonitrile, the title compound was obtained as a white solid (30 mg, 35%). HRMS calculated for C19H18Cl2N4O3 (M+H)+421.0834, found: 421.0834, Rt: 2.94 min. MP: 136° C.

Workup

  1. extractionThe aqueous phase was extracted with ether and AcOEt
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customAfter recrystallisation from acetonitrile

Sources & evidence

ORD record
ord-5c79954fa44d4a8a8fbf49354ab609d1
Source dataset
uspto-grants-2013_07
Patent number
US08486977B2

Reaction notes

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