4-Aminobenzonitrile → HCID 178462390, compound

HRID 480945Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C[Al](C)C.[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[C@@:22]([OH:48])([CH2:42][N:43]1[CH:47]=[N:46][CH:45]=[N:44]1)[C@H:23]([S:25][C@@H:26]1[CH2:31][O:30][C@@H:29]([C:32]2[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=2)[C:35](OC)=[O:36])[O:28][CH2:27]1)[CH3:24]>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:35](=[O:36])[C:34]2[CH:39]=[CH:40][CH:41]=[C:32]([C@H:29]3[O:28][CH2:27][C@H:26]([S:25][C@H:23]([CH3:24])[C@:22]([C:16]4[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=4[F:14])([OH:48])[CH2:42][N:43]4[CH:47]=[N:46][CH:45]=[N:44]4)[CH2:31][O:30]3)[CH:33]=2)=[CH:3][CH:4]=1)#[N:7]

Participants

Reactant 3

HCID 133964-Aminobenzonitrile

HCID 16682925Trimethylaluminum

HCID 178497759HCID 178497759, compound

Product 1

HCID 178462390HCID 178462390, compoundYield 94.4%

Procedure

In the same manner as that described in Example 3(4) a reaction was carried out using commercially available 4-aminobenzonitrile (138 mg, 1.2 mmol), trimethylaluminium (1.08 ml, 1.07M n-hexane solution, 1.2 mmol) and methyl 3-[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 (147 mg, 0.29 mmol), obtained in Example 6(1), and the reaction mixture was treated using a similar procedure to that described in Example 3(4) to afford the title compound (162 mg, yield 94%) as a pale yellow oil which was recrystallized from ethyl acetate-hexane to give pale yellow powdery crystals.

Workup

customobtained in Example 6(1)
additionthe reaction mixture was treated

Sources & evidence

ORD record: ord-10b0d07a178a4efc9b6cb5e69dcbdf52
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653330B2

Reaction notes

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