Toluene → HCID 42606681, compound

HRID 222378Notes

Reaction equation

HRID 222378 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[S:20][C:21]([C:25](OCC)=[O:26])=[C:22]([CH3:24])[N:23]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.[NH4+].[Cl-]>C1COCC1.O.CCOCC>[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[S:20][C:21]([CH2:25][OH:26])=[C:22]([CH3:24])[N:23]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 42605981HCID 42605981, compound

Product 1

HCID 42606681HCID 42606681, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]-4-methyl-1,3-thiazole-5-carboxylate (Example 2) (0.1 g, 0.22 mmol) in THF was added a 1M solution of DIBAL-H in toluene (2.76 mL, 6 eq) and the reaction was stirred to room temperature for 27 hours. Ether was added followed by solid NH4Cl. After 30 min, water was added and the mixture was filtered. The aqueous phase was extracted with ether, dried over sodium sulphate and evaporated. After purification by flash chromatography, eluting with DCM/MeOH 95/5, and crystallisation from acetonitrile, the title compound was obtained as a white solid (3 mg, 3%). HRMS calculated for C16H15Cl2N5O2S (M+H)+412.0402, found: 412.0409, Rt: 2.65 min. MP: 161.8° C.

Workup

  1. waitAfter 30 min
  2. filtrationthe mixture was filtered
  3. extractionThe aqueous phase was extracted with ether
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customAfter purification by flash chromatography
  7. washeluting with DCM/MeOH 95/5, and crystallisation from acetonitrile

Sources & evidence

ORD record
ord-720cb8ea1dd149448db9c6a1bc6801fe
Source dataset
uspto-grants-2012_06
Patent number
US08207204B2

Reaction notes

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