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

HRID 1875783
Notes
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Reaction equation

HRID 1875783 reaction equation
C1(COC2C(C3N(CC4C=C[C:21]([CH2:24][CH2:25][C:26]([OH:28])=O)=[CH:20][CH:19]=4)C4C=C(F)C(F)=CC=4N=3)=CC=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.BrCC1CCCCO1>>[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[N:46]([CH2:19][CH:20]3[CH2:21][CH2:24][CH2:25][CH2:26][O:28]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
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 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 670499992-(4-Chloro-2-methoxy-phenyl)-5,6-difluoro-1-(tetrahydro-pyran-2-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 2-bromomethyl-tetrahydro-pyran (CAS Reg. No. 34723-82-5). Brown powder (39%). MS (Turbo Spray): m/z=393.2 (M+H).

Sources & evidence

ORD record
ord-11720e747db14fa588e38dd8d20f5df3
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08309581B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes