Hydrochloric Acid → HCID 59408990, compound

HRID 1894728Notes

Reaction equation

HRID 1894728 reaction equation
[C:1]1([C:13](=[O:18])[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:20][C:21](=O)[C:22]([C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=O.CC(C)([O-])C.[K+].Cl>O1CCCC1.C(OCC)(=O)C.O>[C:1]1([C:13]([C:14]2[C:15](=[O:16])[NH:17][C:21](=[O:20])[C:22]=2[C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:26][CH:25]=2)=[O:18])[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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 588944Methyl 3-indoleglyoxylateHCID 23665647Potassium tert-butoxideHCID 59408987HCID 59408987, compound

Product 1

HCID 59408990HCID 59408990, compoundYield 78.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-oxo-propionamide (2.0 g, 8.3 mmol) and (1H-indol-3-yl)-oxo-acetic acid methyl ester (1.8 g, 8.8 mmol) in anhydrous tetrahydrofuran (40 ml) at room temperature was added potassium tert-butoxide (26 ml, 26.0 mmol; 1M solution in tetrahydrofuran). After 45 minutes concentrated hydrochloric acid (10 ml) was added. Water (500 ml) was added to the mixture which was then extracted with ethyl acetate (350 ml). The organic layer was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue obtained was sonicated with ethyl acetate (50 ml) to afford 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carbonyl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione as an orange solid (2.58 g). M.p.=>300° C.; 400 MHz 1H NMR (DMSO-d6) δ: 11.99 (s, 1H), 11.12 (s, 1H), 8.18 (s, 1H), 8.13 (s, 1H), 7.93 (m, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.18 (m, 1H), 7.06-7.01 (m, 2H), 6.85 (m, 1H), 4.11 (m, 2H), 2.90 (m, 2H), 2.08 (m, 2H); LCMS: 396 [M+H].

Workup

  1. extractionwas then extracted with ethyl acetate (350 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customevaporated to dryness
  4. customThe residue obtained

Sources & evidence

ORD record
ord-3435aff6aa2342689954b43a3c70a32c
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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