4-(Bromomethyl)oxane → 2-(4-Chloro-2-methoxy-phenyl)-5,6-difluoro-1-(tetrahydro-pyran-4-ylmethyl)-1H-benzoimidazole

HRID 1875787Notes

Reaction equation

HRID 1875787 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11](C3N(CC4C=CC(CCC(O)=O)=CC=4)C4C=C(F)C(F)=CC=4N=3)=[CH:10][CH:9]=CN=2)CC1.[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[N:46](CC3CCCCC3)[C:45]3[CH:54]=[C:55]([F:59])[C:56]([F:58])=[CH:57][C:44]=3[N:43]=2)=[C:38]([O:60][CH2:61]C2C=CC=CC=2Cl)[CH:37]=1.BrCC1CCOCC1>>[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[N:46]([CH2:9][CH:10]3[CH2:1][CH2:4][O:5][CH2:6][CH2:11]3)[C:45]3[CH:54]=[C:55]([F:59])[C:56]([F:58])=[CH:57][C:44]=3[N:43]=2)=[C:38]([O:60][CH3:61])[CH:37]=1

Participants

4

Reactant 3

HCID 27732864-(Bromomethyl)oxaneHCID 510396793-{4-[2-(2-Cyclopropylmethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-phenyl}-propionic acidHCID 582092722-[4-Chloro-2-(2-chloro-benzyloxy)-phenyl]-1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazole2×

Product 1

HCID 670498872-(4-Chloro-2-methoxy-phenyl)-5,6-difluoro-1-(tetrahydro-pyran-4-ylmethyl)-1H-benzoimidazole

Procedure

The title compound was prepared in analogy to Example 19, intermediate b, from 2-(4-chloro-2-methoxy-phenyl)-5,6-difluoro-1H-benzoimidazole (Example 19, intermediate c) and 4-bromomethyl-tetrahydro-pyran (CAS Reg. No. 125552-89-8). Light brown solid (29%). MS (Turbo Spray): m/z=393.3 (M+H).

Sources & evidence

ORD record
ord-107074736d0b43118da2a6de24a923ef
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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