[3-((R)-1-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethylcarbamoyl)-oxetan-3-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester → 3-Amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide

HRID 1404542Notes

Reaction equation

HRID 1404542 reaction equation
ClC1C=C(F)C(C2N=NN(C)N=2)=C(C2C=C(F)C([C@H](NC(=O)C)C)=NC=2)C=1.BrC1C=C(Cl)C=C(F)C=1C1N=NN(C)N=1.ClC1C=C(F)C(C2N=NN(C)N=2)=C(C2C=C(F)C([C@H](N)C)=NC=2)C=1.C1C2C(COC(=O)[NH:83][C:84]3([C:88](=[O:113])[NH:89][C@@H:90]([C:92]4[C:97]([F:98])=[CH:96][C:95]([C:99]5[CH:104]=[C:103]([Cl:105])[CH:102]=[C:101]([F:106])[C:100]=5[C:107]5[N:108]=[N:109][N:110]([CH3:112])[N:111]=5)=[CH:94][N:93]=4)[CH3:91])[CH2:87][O:86][CH2:85]3)C3C(=CC=CC=3)C=2C=CC=1>>[Cl:105][C:103]1[CH:102]=[C:101]([F:106])[C:100]([C:107]2[N:108]=[N:109][N:110]([CH3:112])[N:111]=2)=[C:99]([C:95]2[CH:96]=[C:97]([F:98])[C:92]([C@H:90]([NH:89][C:88]([C:84]3([NH2:83])[CH2:87][O:86][CH2:85]3)=[O:113])[CH3:91])=[N:93][CH:94]=2)[CH:104]=1

Participants

5

Reactant 4

HCID 67979250[3-((R)-1-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethylcarbamoyl)-oxetan-3-yl]-carbamic acid 9H-fluoren-9-ylmethyl esterHCID 67979254N-((R)-1-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-acetamideHCID 684526405-(2-bromo-4-chloro-6-fluoro-phenyl)-2-methyl-2H-tetrazole2×HCID 68714852((1R)-1-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}ethyl)amine

Product 1

HCID 679792733-Amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide

Procedure

The title compound was prepared in analogy to intermediate 1 synthesizing N—((R)-1-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-acetamide in step A (using 5-(2-bromo-4-chloro-6-fluoro-phenyl)-2-methyl-2H-tetrazole (intermediate 11) instead of 3-(2-bromo-4-chloro-6-fluoro-phenyl)-5-methyl-[1,2,4]oxadiazole), (R)-1-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethylamine in step B and [3-((R)-1-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethylcarbamoyl)-oxetan-3-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester in step C. White solid. MS: 450.2 [M+H]+.

Sources & evidence

ORD record
ord-7e7bf93993fd430c8e6919c8af3c0860
Source dataset
uspto-grants-2014_12
Patent number
US08912221B2

Reaction notes

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