1,2-Diamino-4,5-difluorobenzene → 4-[2-(5,6-difluoro-1H-benzoimidazol-2-yl)-benzyloxy]-2-fluoro-benzonitrile

HRID 1875775Notes

Reaction equation

HRID 1875775 reaction equation
C1(COC2C(C3[N:16]([CH2:17][C:18]4[CH:23]=[CH:22][C:21](CCC(O)=O)=[CH:20][CH:19]=4)[C:15]4[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:14]=4[N:13]=3)=CC=CN=2)CC1.[C:35]([C:37]1[CH:53]=[CH:52][C:40]([O:41][CH2:42]C2C=CC=CC=2C(Cl)=O)=[CH:39][C:38]=1[F:54])#[N:36].FC1C=C(N)C(N)=CC=1F>>[F:33][C:31]1[C:30]([F:34])=[CH:29][C:15]2[NH:16][C:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[CH2:42][O:41][C:40]3[CH:52]=[CH:53][C:37]([C:35]#[N:36])=[C:38]([F:54])[CH:39]=3)=[N:13][C:14]=2[CH:32]=1

Participants

4

Reactant 3

HCID 27367551,2-Diamino-4,5-difluorobenzeneHCID 510396793-{4-[2-(2-Cyclopropylmethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-phenyl}-propionic acidHCID 866522902-(4-Cyano-3-fluoro-phenoxymethyl)-benzoyl chloride

Product 1

HCID 670501124-[2-(5,6-difluoro-1H-benzoimidazol-2-yl)-benzyloxy]-2-fluoro-benzonitrile

Procedure

The title compound was prepared in analogy to Example 40, intermediate b, from 2-(4-cyano-3-fluoro-phenoxymethyl)-benzoyl chloride and 4,5-difluoro-benzene-1,2-diamine (CAS Reg. No. 76179-40-3). Light yellow solid (15%). MS (Turbo Spray): m/z=380.2 (M+H).

Sources & evidence

ORD record
ord-17e8440a121b4f8e9e23602be579ad17
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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