1-Hydroxybenzotriazole → N-{[(2S)-4-(3,4-dichlorobenzoyl)morpholin-2-yl]methyl}-2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]acetamide

HRID 2212027Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:17])=[C:11]([CH2:13][C:14]([OH:16])=O)[N:12]=2)=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.Cl.[Cl:50][C:51]1[CH:52]=[C:53]([CH:64]=[CH:65][C:66]=1[Cl:67])[C:54]([N:56]1[CH2:61][CH2:60][O:59][C@@H:58]([CH2:62][NH2:63])[CH2:57]1)=[O:55]>CN(C)C=O>[Cl:50][C:51]1[CH:52]=[C:53]([CH:64]=[CH:65][C:66]=1[Cl:67])[C:54]([N:56]1[CH2:61][CH2:60][O:59][C@@H:58]([CH2:62][NH:63][C:14](=[O:16])[CH2:13][C:11]2[N:12]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[O:9][C:10]=2[CH3:17])[CH2:57]1)=[O:55]

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of Intermediate 12 (0.015 g), 1-hydroxybenzotriazole (0.0097 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.012 g) and N,N-diisopropylethylamine (0.027 ml) in N,N-dimethylformamide (2 ml) was stirred at 20° C. for 10 min. The mixture was treated with Intermediate 31 (0.023 g) and stirred at 20° C. for 96 h. The mixture was applied sequentially to a sulphonic acid ion exchange cartridge (1 g SCX, prewashed with methanol) and IsoluteR aminopropyl solid phase extraction cartridge (1 g), eluting both cartridges with methanol (5 ml). The solvent was removed in vacuo to give the title compound as a yellow gum (0.032 g).

Workup

stirringstirred at 20° C. for 96 h
extractionThe mixture was applied sequentially to a sulphonic acid ion exchange cartridge (1 g SCX, prewashed with methanol) and IsoluteR aminopropyl solid phase extraction cartridge (1 g)
washeluting both cartridges with methanol (5 ml)
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-c510de47deee4a368b306c2999bf19f3
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101882B2

Reaction notes

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