4-Amino-2-chlorobenzonitrile → HCID 178462397, compound

HRID 480956Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.C[Al](C)C.[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[C@@:23]([OH:49])([CH2:43][N:44]1[CH:48]=[N:47][CH:46]=[N:45]1)[C@H:24]([S:26][C@@H:27]1[CH2:32][O:31][C@@H:30]([C:33]2[CH:42]=[CH:41][C:36]([C:37](OC)=[O:38])=[CH:35][CH:34]=2)[O:29][CH2:28]1)[CH3:25]>>[Cl:10][C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][C:5]=1[C:6]#[N:7])[NH:1][C:37](=[O:38])[C:36]1[CH:41]=[CH:42][C:33]([C@H:30]2[O:29][CH2:28][C@H:27]([S:26][C@H:24]([CH3:25])[C@:23]([C:17]3[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=3[F:15])([OH:49])[CH2:43][N:44]3[CH:48]=[N:47][CH:46]=[N:45]3)[CH2:32][O:31]2)=[CH:34][CH:35]=1

Participants

Reactant 3

HCID 887284-Amino-2-chlorobenzonitrile

HCID 16682925Trimethylaluminum

HCID 178497884HCID 178497884, compound

Product 1

HCID 178462397HCID 178462397, compoundYield 90%

Procedure

In the same manner as that described in Example 3(4), a reaction was carried out using commercially available 4-amino-2-chlorobenzonitrile (182 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 (167 mg, yield 90%) as a colorless oil which was recrystallized from ethyl acetate-isopropyl ether to give white powdery crystals.

Workup

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

Sources & evidence

ORD record: ord-dc9dc21d4e404ba9b34844dee65c2921
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653330B2

Reaction notes

Loading…