4,4,4-Trifluorobutylamine → HCID 59354920, compound

HRID 1099443Notes

Reaction equation

HRID 1099443 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].[F:14][C:15]([F:21])([F:20])[CH2:16][CH2:17][CH2:18][NH2:19]>>[F:14][C:15]([F:21])([F:20])[CH2:16][CH2:17][CH2:18][NH:19][C:11]([C:8]1[CH:7]=[CH:6][C:5]([C:3]([OH:2])=[O:4])=[CH:10][N:9]=1)=[O:13]

Participants

3

Reactant 2

HCID 1366454,4,4-TrifluorobutylamineHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acid

Product 1

HCID 59354920HCID 59354920, 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 4,4,4-trifluorobutan-1-amine, 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) 34%; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.16 (t, 1 H), 9.09 (dd, 1 H), 8.44 (dd, 1 H), 8.14 (dd, 1 H), 3.38 (q, 2 H), 2.20-2.36 (m, 2 H), 1.71-1.81 (m, 2 H); MS (ESI) m/z 277[M+H+], m/z 275[M−H+];

Workup

  1. customat 55° C.
  2. customwas first purified by column chromatography
  3. customTotal yield (two steps) 34%

Sources & evidence

ORD record
ord-913d5273001b4458b5b092c9b0161068
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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