3-Isopropoxypropylamine → HCID 14210559, compound

HRID 1099444Notes

Reaction equation

HRID 1099444 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].[CH:14]([O:17][CH2:18][CH2:19][CH2:20][NH2:21])([CH3:16])[CH3:15]>>[CH:14]([O:17][CH2:18][CH2:19][CH2:20][NH:21][C:11]([C:8]1[CH:7]=[CH:6][C:5]([C:3]([OH:2])=[O:4])=[CH:10][N:9]=1)=[O:13])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 761943-IsopropoxypropylamineHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acid

Product 1

HCID 14210559HCID 14210559, 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 3-isopropoxypropylamine, and the second as described for Intermediate example I-98, 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) 22%; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.06 (d, 1 H), 8.99 (t, 1 H), 8.43 (dd, 1 H), 8.13 (dd, 1 H), 3.48-3.56 (m, 1 H), 3.34-3.45 (m, 4 H, obscured by H2O), 1.70-1.80 (m, 2 H), 1.09 (d, 6 H); MS (APPI/APCI) m/z 267[M+H+].

Workup

  1. customwas first purified by column chromatography
  2. customTotal yield (two steps) 22%

Sources & evidence

ORD record
ord-f70f8211a490431f9475e13862e86802
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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