2,2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-hydroxy-2-(4-trimethylstannanyl-phenyl)-ethyl]-acetamide → N-((1R,2S)-1-(4-(6-((1H-imidazol-1-yl)methyl)-pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide

HRID 525511Notes

Reaction equation

HRID 525511 reaction equation
[Cl:1][CH:2]([Cl:21])[C:3]([NH:5][C@H:6]([CH2:19][F:20])[C@H:7]([OH:18])[C:8]1[CH:13]=[CH:12][C:11]([Sn](C)(C)C)=[CH:10][CH:9]=1)=[O:4].[N:22]1([CH2:27][C:28]2[CH:33]=[CH:32][C:31](Br)=[CH:30][N:29]=2)[CH:26]=[CH:25][N:24]=[CH:23]1>>[N:22]1([CH2:27][C:28]2[N:29]=[CH:30][C:31]([C:11]3[CH:12]=[CH:13][C:8]([C@@H:7]([OH:18])[C@H:6]([NH:5][C:3](=[O:4])[CH:2]([Cl:21])[Cl:1])[CH2:19][F:20])=[CH:9][CH:10]=3)=[CH:32][CH:33]=2)[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

3

Reactant 2

HCID 866953832,2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-hydroxy-2-(4-trimethylstannanyl-phenyl)-ethyl]-acetamideHCID 866953922-((1H-imidazol-1-yl)methyl)-5-bromopyridine

Product 1

HCID 86695391N-((1R,2S)-1-(4-(6-((1H-imidazol-1-yl)methyl)-pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide

Procedure

Following the general procedure of Example 6—Step 4 and making non-critical variations but using 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(trimethyl-stannyl)phenyl)propan-2-yl)acetamide and commercially available 2-((1H-imidazol-1-yl)methyl)-5-bromopyridine the title compound is obtained (20 mg): 1H-NMR (400 MHz, DMSO-d6) 4.21-4.24 (m, 1H), 4.27-40.31 (m, 0.5H), 4.38-4.42 (m, 0.5H), 4.55-4.59 (m, 0.5H), 4.67-4.70 (m, 0.5H), 4.89 (t, J=3.6 Hz, 1H), 5.33 (s, 2H), 5.99 (d, J=4.16 Hz, 1H), 6.51 (s, 1H), 6.92 (s, 1H), 7.22 (t, J=3.84 Hz, 2H), 7.46 (d, J=8.2 Hz, 2H), 7.67 (d, J=8.28 Hz, 2H), 7.77 (s, 1H), 8.06-8.08 (d, d J=2.36 Hz, J=8.08 Hz, 1H), 8.63 (d, J=8.84 Hz, 1H), 8.84 (d, J=2.2 Hz, 1H). LC-Ms (m/z): [M+H]=437.1.

Sources & evidence

ORD record
ord-6108c5b3bbeb496e814ff1056a7510aa
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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