Piperonal → 2-Benzo[1,3]dioxol-5-yl-2-[6-chloro-2-(cyclohexyl-methoxy-methyl)-5-fluoro-benzoimidazol-1-yl]-N-cyclohexyl-acetamide

HRID 1170707Notes

Reaction equation

HRID 1170707 reaction equation
[CH2:1]([C:8]1[N:12]([CH:13]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:14]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:15])[C:11]2[CH:29]=[C:30]([Cl:34])[C:31]([F:33])=[CH:32][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([CH:41]=[O:42])CCCCC1.C1C(C=O)=CC2[O:51][CH2:52][O:53]C=2C=1.ClC1C=C(CC(O)=O)C=CC=1.C1(C(OC)C(O)=O)CCCCC1>>[O:51]1[C:26]2[CH:25]=[CH:24][C:23]([CH:13]([N:12]3[C:11]4[CH:29]=[C:30]([Cl:34])[C:31]([F:33])=[CH:32][C:10]=4[N:9]=[C:8]3[CH:1]([CH:2]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]3)[O:42][CH3:41])[C:14]([NH:16][CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)=[O:15])=[CH:28][C:27]=2[O:53][CH2:52]1

Participants

6

Reactant 5

HCID 8438PiperonalHCID 158793-Chlorophenylacetic acidHCID 16275CyclohexanecarboxaldehydeHCID 215051022-Cyclohexyl-2-methoxyacetic acidHCID 673736232-(2-Benzyl-6-chloro-5-fluoro-benzoimidazol-1-yl)-2,N-dicyclohexyl-acetamide

Product 1

HCID 673742652-Benzo[1,3]dioxol-5-yl-2-[6-chloro-2-(cyclohexyl-methoxy-methyl)-5-fluoro-benzoimidazol-1-yl]-N-cyclohexyl-acetamide

Procedure

The title compound was prepared in analogy to Example 1, replacing (2-amino-4,5-difluoro-phenyl)-carbamic acid tert-butyl ester with (2-amino-4-chloro-5-fluoro-phenyl)-carbamic acid tert-butyl ester (([CAS RN 579474-50-3]), Example 47), cyclohexanecarbaldehyde with piperonal ([CAS RN 120-57-0]) and (3-chloro-phenyl)-acetic acid with DL-cyclohexyl-methoxy-acetic acid ([CAS RN 15540-18-8]). MS (ISP): 556.3 [M+H]+.

Sources & evidence

ORD record
ord-f7b11dcd3e304efbab2ccfed3494caf1
Source dataset
uspto-grants-2010_11
Patent number
US07825258B2

Reaction notes

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