Ethanol → HCID 68969554, compound

HRID 1782567Notes

Reaction equation

HRID 1782567 reaction equation
C(C1[CH:36]=[C:35]([CH3:37])[C:6]([C:7]([NH:9][CH2:10][CH2:11][C@H:12]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]([CH2:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][C:33]=3[CH3:34])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)[CH3:13])=[O:8])=[C:5]([CH3:38])[CH:4]=1)#N.[OH-:39].[Na+].[CH3:41][CH2:42][OH:43]>>[CH3:37][C:35]1[CH:36]=[C:41]([CH:4]=[C:5]([CH3:38])[C:6]=1[C:7]([NH:9][CH2:10][CH2:11][C@H:12]([N:14]1[CH2:19][CH2:18][CH:17]([N:20]([CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][C:33]=2[CH3:34])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1)[CH3:13])=[O:8])[C:42]([OH:39])=[O:43]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 57588106HCID 57588106, compound

Product 1

HCID 68969554HCID 68969554, compoundYield 100%

Conditions

Temperature
100 °C

Procedure

To a solution of 4-cyano-2,6-dimethyl-N-((R)-3-{4-[(4-methyl-pyridin-3-ylmethyl)-phenyl-amino]-piperidin-1-yl}-butyl)-benzamide (0.21 g, 0.41 mmol) in EtOH (10 mL) was added 3N NaOH (5 mL) and the resulting colourless solution was stirred at 100° C. for 18 h. The EtOH was removed in vacuo and the pH adjusted to ˜5 before dry loading onto silica gel. Purification by column chromatography on silica gel (8:1:1, CH3CN/MeOH/NH4OH) afforded 3,5-dimethyl-N-((R)-3-{4-[(4-methyl-pyridin-3-ylmethyl)-phenyl-amino]-piperidin-1-yl}-butyl)-terephthalamic acid (0.23 g, 100%) as a white solid. 1H NMR (CD3OD) δ 1.43 (d, 3H, J=8 Hz), 1.91 (m, 1H), 2.14 (m, 3H), 2.22 (m, 1H), 2.32 (s, 6H), 2.41 (s, 2H), 3.34 (s, 5H), 3.45 (m, 4H), 3.53 (m, 1H), 4.20 (m, 1H), 4.48 (s, 2H), 6.79 (m, 3H), 7.19 (m, 3H), 7.66 (m, 2H), 8.23 (m, 2H).

Workup

  1. customThe EtOH was removed in vacuo
  2. custombefore dry loading onto silica gel
  3. customPurification by column chromatography on silica gel (8:1:1, CH3CN/MeOH/NH4OH)

Sources & evidence

ORD record
ord-16b1df0fd357424aa4c0d37b5488b6f8
Source dataset
uspto-grants-2009_03
Patent number
US07498346B2

Reaction notes

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