Cyclopropanemethanol → HCID 21109686, compound

HRID 1929911Notes

Reaction equation

HRID 1929911 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=[O:10])[CH:5]=[N:6][C:7]=1Cl.[OH:12][CH2:13][CH:14]1[CH2:16][CH2:15]1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.[NH2:27][CH2:28][C:29]([CH3:35])([OH:34])[C:30]([F:33])([F:32])[F:31]>>[CH:14]1([CH2:13][O:12][C:7]2[C:2]([C:21]3[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=3)=[CH:3][C:4]([C:9]([NH:27][CH2:28][C@:29]([OH:34])([CH3:35])[C:30]([F:33])([F:32])[F:31])=[O:11])=[CH:5][N:6]=2)[CH2:16][CH2:15]1.[CH:14]1([CH2:13][O:12][C:7]2[C:2]([C:21]3[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=3)=[CH:3][C:4]([C:9]([NH:27][CH2:28][C:29]([OH:34])([CH3:35])[C:30]([F:33])([F:32])[F:31])=[O:10])=[CH:5][N:6]=2)[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 75644CyclopropanemethanolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 2856454-Fluorophenylboronic acidHCID 136207593-Amino-1,1,1-trifluoro-2-methylpropan-2-ol

Product 2

HCID 21109686HCID 21109686, compoundHCID 24856920HCID 24856920, compound

Procedure

The title compound was synthesized in analogy to Example 31, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, hydroxymethylcyclopropan, 4-fluorophenylboronic acid and 3-amino-1,1,1-trifluoro-2-methyl-propan-2-ol (CAN [354-68-7]) as starting materials to yield (RS)-6-cyclopropylmethoxy-N-(3,3,3-trifluoro-2-hydroxy-2-methyl-propyl)-5-(4-fluoro-phenyl)-nicotinamide. The two enantiomers were separated by column chromatography on chiral phase. White solid, MS (ISP) 413.1 (M+H)+.

Sources & evidence

ORD record
ord-99ee589574b7446d84dd94864ae0131a
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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