5-(Methoxycarbonyl)pyridine-2-carboxylic acid → HCID 25116533, compound

HRID 1099442Notes

Reaction equation

HRID 1099442 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].Cl.[F:15][C:16]1([F:23])[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1>>[F:15][C:16]1([F:23])[CH2:21][CH2:20][CH:19]([NH:22][C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:2])=[O:4])=[CH:10][N:9]=2)=[O:13])[CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 231506694,4-Difluorocyclohexan-1-amine hydrochloride

Product 1

HCID 25116533HCID 25116533, compound

Procedure

The title compound was synthesized in two steps. The first as described for Intermediate example I-97, starting from 5-(methoxycarbonyl)pyridine-2-carboxylic acid and 4,4-difluorocyclohexylamine hydrochlorid, and the second as described for Intermediate example I-98 at 55° C., starting from the product received in the first step which was first purified by column chromatography using a gradient of ethyl acetate in heptane. Total yield (two steps) 65%; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.08 (dd, 1 H), 8.89 (d, 1 H), 8.43 (dd, 1 H), 8.13 (dd, 1 H), 3.95-4.07 (m, 1 H), 1.68-2.11 (m, 8 H); MS (ESI) m/z 285[M+H+], m/z 283[M−H+];

Workup

  1. customat 55° C.
  2. customwas first purified by column chromatography
  3. customTotal yield (two steps) 65%

Sources & evidence

ORD record
ord-9a28de30708449cfb8c20ab76988d942
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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