Hydrochloric Acid → HCID 22036817, compound

HRID 1789977Notes

Reaction equation

[CH3:1][C:2]1([CH3:25])[N:11]2[C:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][C:13]=3[C:9]3[C:10]2=[C:5]([CH:6]=[CH:7][CH:8]=3)[N:4]([CH3:23])[C:3]1=O.Cl.O>C1COCC1>[CH2:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][C:12]2[N:11]3[C:10]4[C:9]([C:13]=2[CH2:14]1)=[CH:8][CH:7]=[CH:6][C:5]=4[N:4]([CH3:23])[CH2:3][C:2]3([CH3:1])[CH3:25])=[O:19])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 1,1,3-trimethyl-2-oxo-2,3,9,10-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (240 mg, 0.7 mmol) in THF (20 mL) at 25° C. was added BH3/THF complex (0.7 mL, 0.7 mmol). The mixture was stirred at 80° C. for 5 hours then cooled to rt and added 6N HCl (10 mL) with stirred for another 1 hr. About 30 mL of H2O was added and then was extracted with EtOAc (2×30 mL). The combined extracts were dried over magnesium sulfate, concentrated, and purified by flash chromatography to give ethyl-1,1,3-trimethyl-2,3,9,10-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate as an oil (152 mg, 66%). MS [M+H]+ 327. 1H NMR (CDCl3, 300 MHz) δ 7.01 (t, 1H, J=7.7 Hz), 6.97 (d, 1H, J=7.7 Hz), 6.41 (d, 1H, J=7.7 Hz), 4.68 (s, 2H), 4.23 (m, 2H), 3.84 (m, 2H), 3.11 (m, 2H), 2.99 (s, 3H), 1.54 (s, 6H), 1.27 (t, 3H, J=7.3 Hz) ppm.

Workup

temperaturethen cooled to rt
stirringwith stirred for another 1 hr
extractionwas extracted with EtOAc (2×30 mL)
dry with materialThe combined extracts were dried over magnesium sulfate
concentrationconcentrated
custompurified by flash chromatography

Sources & evidence

ORD record: ord-2e890b6654fc4022af6146dc53482ebb
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071186B2

Reaction notes

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