Ethyl 4-aminocyclohexanecarboxylate → 4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester

HRID 1947015Notes

Reaction equation

CS([C:4]1[N:9]=[C:8]([N:10]2[C:18]3[C:13](=[C:14]([O:19][CH2:20][CH2:21][CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)[CH:7]=[CH:6][N:5]=1)=O.[CH2:27]([O:29][C:30]([CH:32]1[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34][CH2:33]1)=[O:31])[CH3:28]>O1CCOCC1.O>[CH2:27]([O:29][C:30]([CH:32]1[CH2:37][CH2:36][CH:35]([NH:38][C:4]2[N:9]=[C:8]([N:10]3[C:18]4[C:13](=[C:14]([O:19][CH2:20][CH2:21][CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:15]=[CH:16][CH:17]=4)[CH:12]=[CH:11]3)[CH:7]=[CH:6][N:5]=2)[CH2:34][CH2:33]1)=[O:31])[CH3:28]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1-(2-methanesulfinyl-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (25 g, 64 mM) and 4-amino-cyclohexanecarboxylic acid ethyl ester (16.3 g, 95.3 mM) in dioxane (400 mL) and heated at 110° C. for approximately 5 h. The solution was concentrated in vacuo to give a white residue. The residue was suspended in H2O, filtered and washed in H2O, and dried at 60° C. in vacuo to yield 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester (31.7 g, 99.7%).

Workup

concentrationThe solution was concentrated in vacuo
customto give a white residue
filtrationfiltered
washwashed in H2O
customdried at 60° C. in vacuo

Sources & evidence

ORD record: ord-17a25a71b0104b20ac4c77bffbdea06a
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399462B2

Reaction notes

Loading…