Potassium Carbonate → HCID 58216344, compound

HRID 1426073Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of compound (6-chloro-5-nitro-pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)-amine (400 mg, 1.22 mmol), 4-(4-trifluoromethoxy-phenoxy)-piperidine (399 mg, 1.34 mmol) and potassium carbonate (336 mg, 2.44 mmol) in DMF (8 ml) was heated in an oil bath at 60° C. for 2 hours. The crude mixture was cooled to 0° C. and quenched with water. The solid was filtered off, rinsed with water and dried in vacuum oven to give product B119 as a yellow solid (604 mg, 90%). 1HNMR (CDCl3, 400 MHz) d 2.01-2.08 (m, 4H), 3.06 (s, 3H), 3.64-3.66 (m, 2H), 3.73-3.75 (m, 2H), 4.62-4.66 (m, 1H), 6.93 (d, 2H), 7.17 (d, 2H), 7.93 (dd, 4H), 8.21 (s, 1H), 10.2 (s, 1H). Exact mass calculated for C23H22F3N5O6S 553.1, found 554.3 (MH+).

Workup

customquenched with water
filtrationThe solid was filtered off
washrinsed with water
customdried in vacuum oven
customto give product

Sources & evidence

ORD record: ord-4cbbb385e13d467582815c031c5153da
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933083B2

Reaction notes

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