p-Toluidine → HCID 178426564, compound

HRID 480954Notes

Reaction equation

HRID 480954 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C[Al](C)C.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C@@:21]([OH:47])([CH2:41][N:42]1[CH:46]=[N:45][CH:44]=[N:43]1)[C@H:22]([S:24][C@@H:25]1[CH2:30][O:29][C@@H:28]([C:31]2[CH:40]=[CH:39][C:34]([C:35](OC)=[O:36])=[CH:33][CH:32]=2)[O:27][CH2:26]1)[CH3:23]>>[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C@@:21]([OH:47])([CH2:41][N:42]1[CH:46]=[N:45][CH:44]=[N:43]1)[C@H:22]([S:24][C@@H:25]1[CH2:30][O:29][C@@H:28]([C:31]2[CH:32]=[CH:33][C:34]([C:35]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=3)=[O:36])=[CH:39][CH:40]=2)[O:27][CH2:26]1)[CH3:23]

Participants

4

Reactant 3

HCID 7813p-ToluidineHCID 16682925TrimethylaluminumHCID 178497884HCID 178497884, compound

Product 1

HCID 178426564HCID 178426564, compoundYield 96%

Procedure

In the same manner as that described in Example 3(4), a reaction was carried out using commercially available p-toluidine (128 mg, 1.2 mmol), trimethylaluminium (1.1 ml, 1.07M n-hexane solution, 1.2 mmol) and methyl 4-[trans-5-[[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]thio]-1,3-dioxan-2-yl]benzoate (150 mg, 0.30 mmol), obtained in Example 12(1), and the reaction mixture was treated using a similar procedure to that described in Example 3(4) to afford the title compound (166 mg, yield 96%) as a pale yellow oil which was recrystallized from ethyl acetate-hexane to give white powdery crystals.

Workup

  1. customobtained in Example 12(1)
  2. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-ed148470c353432cafefa97856a70d2c
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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