Piperidine → ethyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylate

HRID 655739Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:18]3[CH2:23][CH2:22][C@@H:21]([NH:24][C:25]([C:27]4[NH:28][C:29]([CH3:34])=[C:30]([Cl:33])[C:31]=4[Cl:32])=[O:26])[C@@H:20]([O:35][CH2:36][CH3:37])[CH2:19]3)[S:11][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:6][CH:7]=1.[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.C(N(CC)C(C)C)(C)C>CN1CCCC1>[Cl:32][C:31]1[C:30]([Cl:33])=[C:29]([CH3:34])[NH:28][C:27]=1[C:25]([NH:24][C@@H:21]1[CH2:22][CH2:23][N:18]([C:10]2[S:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([C:5]3[CH:4]=[N:3][C:2]([N:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)=[CH:7][N:6]=3)[N:9]=2)[CH2:19][C@@H:20]1[O:35][CH2:36][CH3:37])=[O:26]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of ethyl 4-(5-chloropyrazin-2-yl)-2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl]-1,3-thiazole-5-carboxylate (Example 66, 120 mg, 0.204 mmol) and piperidine (87 mg 1.023 mmol) in N-methyl pyrrolidine was added N,N-diisopropyl ethylamine; the reaction mixture was then stirred over night at 80° C. The reaction mixture was cooled to room temperature and poured on to ice cold water. The precipitated product was collected by filtration and dried to afford 120 mg (92%) of ethyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylate.

Workup

temperatureThe reaction mixture was cooled to room temperature
additionpoured on to ice cold water
filtrationThe precipitated product was collected by filtration
customdried

Sources & evidence

ORD record: ord-2c595d307edb4285b7e3eaccddb3d05b
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071605B2

Reaction notes

Loading…