Cyclopropanemethanol → 6-Cyclopropylmethoxy-5-(4-fluoro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide

HRID 1766488Notes

Reaction equation

CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[N:6][CH:5]=1.[CH:13]1([CH2:16][OH:17])[CH2:15][CH2:14]1.[F:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.[NH2:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]1[OH:35]>>[CH:13]1([CH2:16][O:17][C:7]2[C:8]([C:22]3[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=3)=[CH:9][C:4]([C:3]([NH:28][C@@H:29]3[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]3[OH:35])=[O:12])=[CH:5][N:6]=2)[CH2:15][CH2:14]1

Participants

Reactant 4

HCID 75644Cyclopropanemethanol

HCID 2856454-Fluorophenylboronic acid

HCID 735777(1R,2R)-2-Aminocyclohexanol

HCID 2764313Methyl 5-bromo-6-chloronicotinate

Product 1

HCID 119516556-Cyclopropylmethoxy-5-(4-fluoro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 23, using 5-bromo-6-chloro-nicotinic acid methyl ester, cyclopropylmethanol (commercially available), 4-fluorophenylboronic acid (commercially available) and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials. MS (m/e): 385.3 (MH+).

Workup

customdescribed for the preparation of Example 23

Sources & evidence

ORD record: ord-6e57b5021d2b46cfb57b8ba98072d834
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07229999B2

Reaction notes

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