Cyclopropanemethanol → HCID 24856635, compound

HRID 1929875Notes

Reaction equation

HRID 1929875 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]([F:31])([F:30])[O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.[NH2:32][CH2:33][C:34]([CH:37]1[CH2:39][CH2:38]1)([OH:36])[CH3:35]>>[CH:37]1([C@@:34]([OH:36])([CH3:35])[CH2:33][NH:32][C:3](=[O:12])[C:4]2[CH:9]=[C:8]([C:24]3[CH:25]=[CH:26][C:21]([O:20][C:19]([F:31])([F:30])[F:18])=[CH:22][CH:23]=3)[C:7]([O:17][CH2:16][CH:13]3[CH2:15][CH2:14]3)=[N:6][CH:5]=2)[CH2:39][CH2:38]1

Participants

5

Reactant 4

HCID 75644CyclopropanemethanolHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 211096921-Amino-2-cyclopropylpropan-2-ol

Product 1

HCID 24856635HCID 24856635, compound

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 43, using 5-bromo-6-chloro-nicotinic acid methyl ester, cyclopropylmethanol (commercially available), 4-trifluoromethoxyphenylboronic acid (commercially available) and rac-1-amino-2-cyclopropyl-propan-2-ol (commercially available) as starting materials. The two enantiomers were separated by column chromatography on chiral phase. MS (ISP): 451.1 (M+H+).

Workup

  1. customdescribed for the preparation of Example 43
  2. customThe two enantiomers were separated by column chromatography on chiral phase

Sources & evidence

ORD record
ord-94e18d55aae046119fc52f5c3daf328e
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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