[5-(4-Fluoro-phenyl)-2-(3-methoxy-2-triisopropylsilanyloxy-phenyl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanone → 6-{2-Cyanomethoxy-3-[5-(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-pyridine-2-carboxylic acid ethyl ester

HRID 1046953Notes

Reaction equation

HRID 1046953 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12]C(C3C=CC=C(OC)C=3O[Si](C(C)C)(C(C)C)C(C)C)[N:10]([C:32]([C:34]3[C:39]([F:40])=[CH:38][C:37]([F:41])=[CH:36][C:35]=3[F:42])=[O:33])[N:9]=2)=[CH:4][CH:3]=1.[CH2:43]([O:45][C:46]([C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([CH2:54][O:55][C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([CH:62]=O)[C:57]=2[O:64][CH2:65][C:66]#[N:67])[N:49]=1)=[O:47])[CH3:44]>>[CH2:43]([O:45][C:46]([C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([CH2:54][O:55][C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([CH:62]3[N:10]([C:32](=[O:33])[C:34]4[C:35]([F:42])=[CH:36][C:37]([F:41])=[CH:38][C:39]=4[F:40])[N:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[S:12]3)[C:57]=2[O:64][CH2:65][C:66]#[N:67])[N:49]=1)=[O:47])[CH3:44]

Participants

3

Reactant 2

HCID 67279689[5-(4-Fluoro-phenyl)-2-(3-methoxy-2-triisopropylsilanyloxy-phenyl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanoneHCID 86637602HCID 86637602, compound

Product 1

HCID 580257896-{2-Cyanomethoxy-3-[5-(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-pyridine-2-carboxylic acid ethyl ester

Procedure

6-{2-Cyanomethoxy-3-[5-(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-pyridine-2-carboxylic acid ethyl ester is prepared in a similar manner as described for [5-(4-fluoro-phenyl)-2-(3-methoxy-2-triisopropylsilanyloxy-phenyl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanone in example 3 using 6-(2-cyanomethoxy-3-formyl-phenoxymethyl)-pyridine-2-carboxylic acid ethyl ester. 1H NMR (400 MHz, CDCl3) δ 8.1 (d, J=7.9 Hz, 1H), 7.94 (t, J=7.9 Hz, 1H), 7.76 (d, J=7.5 Hz, 1H), 7.54-7.58 (m, 3H), 7.05-7.14 (m, 3H), 7.01 (d, J=7.3 Hz, 1H), 6.96 (d, J=8.9 Hz, 1H), 6.76 (t, J=8.5 Hz, 2H), 5.4 (s, 2H), 5.12 (d, J=4.4 Hz, 2H), 4.5 (q, J=7.2 Hz, 2H), 1.45 (t, J=7.3 Hz, 3H); LC/MS (ES+): 651.2 (M+1)+.

Sources & evidence

ORD record
ord-2944494365464c9481cdcb23df555a5e
Source dataset
uspto-grants-2013_10
Patent number
US08569345B2

Reaction notes

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