4-Aminobenzonitrile → HCID 178462395, compound

HRID 480944Notes

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:49])([CH2:43][N:44]1[CH:48]=[N:47][CH:46]=[N:45]1)[C@H:23]([S:25][C@@H:26]1[CH2:31][O:30][C@@H:29]([C:32]2[CH:41]=[CH:40][C:35]([C:36](OC)=[O:37])=[CH:34][C:33]=2[F:42])[O:28][CH2:27]1)[CH3:24]>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:36](=[O:37])[C:35]2[CH:40]=[CH:41][C:32]([C@H:29]3[O:30][CH2:31][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:49])[CH2:43][N:44]4[CH:48]=[N:47][CH:46]=[N:45]4)[CH2:27][O:28]3)=[C:33]([F:42])[CH:34]=2)=[CH:3][CH:4]=1)#[N:7]

Participants

Reactant 3

HCID 133964-Aminobenzonitrile

HCID 16682925Trimethylaluminum

HCID 178497886HCID 178497886, compound

Product 1

HCID 178462395HCID 178462395, compoundYield 75%

Procedure

In the same manner as that described in Example 3(4) a reaction was carried out using commercially available 4-aminobenzonitrile (98 mg, 0.83,mmol), trimethylaluminium (0.78 ml, 1.07M n-hexane solution, 0.83 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]-3-fluorobenzoate (109 mg, 0.21 mmol) obtained in Example 5(2) and the reaction mixture was treated using a similar procedure to that described in Example 3(4) to give the title compound (95 mg, yield 75%) as a colorless oil which was recrystallized from ethyl acetate-hexane to give white powdery crystals.

Workup

additionthe reaction mixture was treated

Sources & evidence

ORD record: ord-d2acf36c55e844f4ad4cacb3b4c6f39b
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653330B2

Reaction notes

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