p-Toluenesulfonic acid → HCID 49820827, compound

HRID 1692867Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([N:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH2:28]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C>[N:27]1([C:2]2[N:3]=[C:4]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:5]3[S:10][C:9]([CH2:11][N:12]4[CH2:17][CH2:16][CH:15]([N:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]4)=[CH:8][C:6]=3[N:7]=2)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 150 °C

Procedure

A microwave vessel was charged with [1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-yl]-dimethyl-amine (0.2 g), indoline (0.12 g), p-toluenesulfonic acid (0.01 g), and DMF (3 mL). The vessel was sealed and heated at 150° C. under microwave irradiation for 4 h. The reaction mixture was cooled to room temperature and the solid precipitate was filtered and purified by chromatography (silica, 0 to 20% of a 49:1 MeOH:NH4OH mixture in dichloromethane) to furnish the title compound (0.09 g, 38%) as an off-white solid. MS m/e 479 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.36-1.65 (m, 2H) 1.85 (d, J=11.30 Hz, 2H) 2.06 (t, J=10.74 Hz, 2H) 2.44 (br. s., 6H) 2.97 (d, J=11.30 Hz, 2H) 3.12 (t, J=8.48 Hz, 3H) 3.67-3.93 (m, 10H) 4.17 (t, J=8.67 Hz, 2H) 6.84 (t, J=7.35 Hz, 1H) 7.03-7.29 (m, 3H) 8.31 (d, J=7.91 Hz, 1H).

Workup

customThe vessel was sealed
temperatureThe reaction mixture was cooled to room temperature
filtrationthe solid precipitate was filtered
custompurified by chromatography (silica, 0 to 20% of a 49:1 MeOH:NH4OH mixture in dichloromethane)

Sources & evidence

ORD record: ord-e9ddd934d4354419abf2e823c2d93062
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158625B2

Reaction notes

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