Triethylamine → HCID 59300508, compound

HRID 603462Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:15]=[CH:14][N:13]=[C:12](Cl)[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.FC(F)(F)C(O)=O.[NH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[C@H:34]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:33][CH2:32]2.C(N(CC)CC)C>CC#N.O1CCOCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH:24][CH2:25][CH2:26][CH2:27][O:28][C:29]4[CH:30]=[C:31]5[C:35](=[CH:36][CH:37]=4)[C@H:34]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:33][CH2:32]5)[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

4-(1,3-Benzodioxol-5-yl)-2-chloropyrimidine (Example 290, 108 mg, 0.46 mmol) and ethyl [(1S)-5-(3-aminopropoxy)-2,3-dihydro-1H-inden-1-yl]acetate trifluoroacetate (Example 263, 277 mg, 0.418 mmol) were dissolved in MeCN (2.6 mL) and 1,4-dioxane (2.6 mL), after which triethylamine (0.175 mL) was added. The reaction mixture was stirred at 90° C. for 18 h, and then cooled to rt. The solvents removed under reduced pressure, and the residue was purified by silica gel flash chromatography (1:2 EtOAc/Hexanes) to give the title compound (136 mg, 69%). 1H NMR (400 MHz, CDCl3): δ 1.32 (t, 3H), 1.70-1.79 (m, 1H), 2.15-2.20 (m, 2H), 2.30-2.51 (m, 2H), 2.73 (dd, 1H), 2.80-2.95 (m, 2H), 3.55-3.64 (m, 1H), 3.74 (q, 2H), 4.14 (t, 2H), 4.22 (q, 2H), 5.42 (s, 1H), 6.01 (s, 1H), 6.65 (d, 1H), 6.75 (s, 1H), 6.90 (d, 2H), 7.05 (d, 1H), 7.20 (d, 2H), 8.15 (s, 1H), 8.25 (d, 1H); LC-MS: RT=2.80 min, (M+H)+ 506.3.

Workup

temperaturecooled to rt
customThe solvents removed under reduced pressure
customthe residue was purified by silica gel flash chromatography (1:2 EtOAc/Hexanes)

Sources & evidence

ORD record: ord-36db90f48e754655b6800fb617c49c3a
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906653B2

Reaction notes

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