1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-chloro-2,4-dimethyl-N-(3-{4-[(thiazol-4-ylmethyl)-amino]-piperidin-1-yl}-butyl)-nicotinamide

HRID 1711138Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][CH2:13][C:14]2[N:15]=[CH:16][S:17][CH:18]=2)[CH2:8][CH2:7]1)[CH3:5].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:40][C:41]1[CH:49]=[C:48]([CH3:50])[C:44]([C:45](O)=[O:46])=[C:43]([CH3:51])[N:42]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:40][C:41]1[CH:49]=[C:48]([CH3:50])[C:44]([C:45]([NH:1][CH2:2][CH2:3][CH:4]([N:6]2[CH2:11][CH2:10][CH:9]([NH:12][CH2:13][C:14]3[N:15]=[CH:16][S:17][CH:18]=3)[CH2:8][CH2:7]2)[CH3:5])=[O:46])=[C:43]([CH3:51])[N:42]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Following general procedure E: to a stirred solution of [1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-thiazol-4-ylmethyl-amine (0.320 g. 1.19 mmol), EDCI (0.252 g, 1.31 mmol) and HOBt (0.177 g, 1.31 mmol) in DMF (5 ml) was added 6-chloro-2,4-dimethyl-nicotinic acid (0.243 g, 1.31 mmol) followed by DIPEA (343 μL, 1.78 mmol) and the resulting mixture was stirred at 25° C. for 16 hours. Standard workup and purification by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 93:5:2) afforded 6-chloro-2,4-dimethyl-N-(3-{4-[(thiazol-4-ylmethyl)-amino]-piperidin-1-yl}-butyl)-nicotinamide (0.42 g, 81%) as a colorless oil.

Workup

customStandard workup and purification by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 93:5:2)

Sources & evidence

ORD record: ord-81ae00c000864311b95f5c53cf1c20ff
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790747B2

Reaction notes

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