Cyclohexanemethylamine → HCID 21865077, compound

HRID 857681Notes

Reaction equation

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

Participants

Reactant 2

HCID 76688Cyclohexanemethylamine

HCID 21865127HCID 21865127, compound

Product 1

HCID 21865077HCID 21865077, compound

Procedure

According to the procedure described in Example 188, 7-[6-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-pyrimidin-4-yloxy]-quinoline (Example 187) (110 mg, 0.27 mmol) and cyclohexanemethylamine (43 μL, 0.33 mmol, Aldrich), after purification by silica gel chromatography (gradient, 0 to 3% MeOH/CH2Cl2) and then preparative TLC (4% MeOH/ CH2Cl2), provided the title compound as a yellow solid. MP: 151–152° C. MS (ESI, pos. ion) m/z: 480 (M+1).

Workup

customafter purification by silica gel chromatography (gradient, 0 to 3% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-fb226e8d1f574aeba97444c9bddb92ca
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144888B2

Reaction notes

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