1-(4-((2H-1,2,3-triazol-4-yl)methoxy)-3-fluorophenyl)-1H-tetrazole → 5-Ethyl-2-((trans)-3-fluoro-4-(4-((2-fluoro-4-(1H-tetrazol-1-yl)phenoxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)pyrimidine

HRID 1928603Notes

Reaction equation

HRID 1928603 reaction equation
[N:1]1[NH:2][N:3]=[C:4]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:18]=[N:17][N:16]=[N:15]3)=[CH:10][C:9]=2[F:19])[CH:5]=1.[CH2:20]([C:22]1[CH:23]=[N:24][C:25]([N:28]2[CH2:33][CH2:32][C@H:31](O)[C@H:30]([F:35])[CH2:29]2)=[N:26][CH:27]=1)[CH3:21]>>[CH2:20]([C:22]1[CH:23]=[N:24][C:25]([N:28]2[CH2:33][CH2:32][C@@H:31]([N:2]3[N:3]=[C:4]([CH2:6][O:7][C:8]4[CH:13]=[CH:12][C:11]([N:14]5[CH:18]=[N:17][N:16]=[N:15]5)=[CH:10][C:9]=4[F:19])[CH:5]=[N:1]3)[C@H:30]([F:35])[CH2:29]2)=[N:26][CH:27]=1)[CH3:21]

Participants

3

Reactant 2

HCID 577084341-(4-((2H-1,2,3-triazol-4-yl)methoxy)-3-fluorophenyl)-1H-tetrazole2×HCID 68985294cis-1-(5-Ethylpyrimidin-2-yl)-3-fluoropiperidin-4-ol2×

Product 1

HCID 689871095-Ethyl-2-((trans)-3-fluoro-4-(4-((2-fluoro-4-(1H-tetrazol-1-yl)phenoxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)pyrimidine

Procedure

The title compound was synthesized using 1-(4-((2H-1,2,3-triazol-4-yl)methoxy)-3-fluorophenyl)-1H-tetrazole (Intermediate 16) and cis-1-(5-ethylpyrimidin-2-yl)-3-fluoropiperidin-4-ol (Intermediate 17) in a manner similar to that described in Example 29. 1H NMR (CDCl3): δ 8.92 (1H, s), 8.21 (2H, s), 7.76 (1H, s), 7.51 (1H, dd), 7.41 (1H, d), 7.26 (1H, m), 5.31 (2H, s), 5.17 (1H, m), 5.03 (1H, m), 4.83 (2H, m), 3.11 (2H, m), 2.50 (2H, q), 2.22 (2H, m), 1.22 (3H, t).

Sources & evidence

ORD record
ord-21168c85ff234b4897879ab7019d2942
Source dataset
uspto-grants-2012_05
Patent number
US08183381B2

Reaction notes

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