Trifluoroacetic acid → 3-morpholino-6-(2-((tetrahydro-2H-pyran-4-yl)methyl)phenyl)quinolin-2-amine

HRID 1028957Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

(2-(2-Amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanol (0.085 g, 0.203 mmol, see Example 12) was dissolved in DCM (20 mL) and treated with triethylsilane (1.0 mL, 6.26 mmol) and TFA (2.0 mL, 26.9 mmol). The mixture was heated to 70° C. for 30 min after which analysis showed the reduction was complete. The solution was evaporated to dryness under reduced pressure. The crude was partitioned between water (10 mL), saturated sodium bicarbonate (10 mL) and DCM (20 mL). The organic layer was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (0-10% methanol in DCM gradient) gave the desired 3-morpholino-6-(2-((tetrahydro-2H-pyran-4-yl)methyl)phenyl)quinolin-2-amine. MS (ESI, pos. ion) m/z: 404 (M+1).

Workup

customThe solution was evaporated to dryness under reduced pressure
customThe crude was partitioned between water (10 mL), saturated sodium bicarbonate (10 mL) and DCM (20 mL)
dry with materialThe organic layer was dried with magnesium sulfate
customevaporated to dryness under reduced pressure
customPurification

Sources & evidence

ORD record: ord-a5de151947f241b49b806b1543e4f1c4
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735384B2

Reaction notes

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