Hydrochloric Acid → HCID 59408988, compound

HRID 1894726Notes

Reaction equation

HRID 1894726 reaction equation
[C:1]1([CH2:13][CH2:14][C:15]([NH2:17])=[O:16])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.C[O:19][C:20](=O)[C:21]([C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=O.CC(C)([O-])C.[K+].Cl>O1CCCC1.C(OCC)(=O)C>[C:1]1([CH2:13][C:14]2[C:15](=[O:16])[NH:17][C:20](=[O:19])[C:21]=2[C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][CH:24]=2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 588944Methyl 3-indoleglyoxylateHCID 23665647Potassium tert-butoxideHCID 59408996HCID 59408996, compound

Product 1

HCID 59408988HCID 59408988, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-propionamide (249 mg, 1.1 mmol) and (1H-indol-3-yl)-oxo-acetic acid methyl ester (244 mg, 1.2 mmol) in anhydrous tetrahydrofuran (10 ml) at 0° C. was added potassium tert-butoxide (4.36 ml, 4.36 mmol; 1M in tetrahydrofuran). The mixture was allowed to warm to room temperature for 2 hours. Concentrated hydrochloric acid (4 ml) was added and the mixture stirred at room temperature for a further 30 minutes. The mixture was poured into ethyl acetate (250 ml), washed with water (750 ml) and purified by flash column chromatography (SiO2, 30 to 40% EtOAc in hexanes) to afford 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-ylmethyl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione as an orange foam (226 mg). 400 MHz 1H NMR (CDCl3) δ: 8.54 (s, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.53 (d, J=3.2 Hz, 1H), 7.42 (m, 1H), 7.3-7.25 (m, 1H), 7.21-7.17 (m, 1H), 7.09 (dd, J=1.6 and 7.2 Hz, 1H), 6.92-6.86 (m, 2H), 4.15-4.04 (m, 4H), 2.95 (t, J=6.4 Hz, 2H), 2.22-2.16 (m, 2H); LCMS: 382 [M+H].

Workup

  1. washwashed with water (750 ml)
  2. custompurified by flash column chromatography (SiO2, 30 to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b3c5be16c98f43f985161738dfae2fae
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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