Hydrochloric Acid → HCID 59404393, compound

HRID 1873671Notes

Reaction equation

HRID 1873671 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[C:18](=[O:41])[N:19](C(OC(C)(C)C)=O)[CH2:20][C:21]=2[C:22]2[C:32]3=[C:33]4[C:28](=[CH:29][CH:30]=[CH:31]3)[CH2:27][CH2:26][CH2:25][N:24]4[CH:23]=2)=[CH:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[C:22]1([C:21]2[CH2:20][NH:19][C:18](=[O:41])[C:17]=2[C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8][CH:9]=2)[C:32]2=[C:33]3[C:28](=[CH:29][CH:30]=[CH:31]2)[CH2:27][CH2:26][CH2:25][N:24]3[CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59404401HCID 59404401, compound

Product 1

HCID 59404393HCID 59404393, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-[1-tert-butoxycarbonyl-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-indole-1-carboxylic acid tert-butyl ester (408 mg, 738 μmol) and 4M HCl in dioxane (15 mL) was shaken at room temperature for 16 h. The solvent was removed and the residue partitioned between EtOAc and 2N NaOH. The organics were concentrated and the residue purified by flash column chromatography (SiO2, DCM/MeOH). The solid obtained was recrystallised from DCM to afford 4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-(1H-indol-3-yl)-1,5-dihydro-pyrrol-2-one as a pale yellow solid (159 mg, 61%). M.p.=260-262° C.; 1H NMR (400 MHz, DMSO-d6) δ: 11.22 (s, 1H), 8.16 (s, 1H), 7.44-7.39 (m, 2H), 7.31 (s, 1H), 7.05-6.95 (m, 3H), 6.82-6.74 (m, 3H), 4.51 (s, 2H), 4.00 (t, J=5.6 Hz, 2H), 2.86 (t, J=6.0 Hz, 2H), 2.05 (t, J=5.2 Hz, 2H). LCMS: m/e 354.12 [M+H].

Workup

  1. customThe solvent was removed
  2. customthe residue partitioned between EtOAc and 2N NaOH
  3. concentrationThe organics were concentrated
  4. customthe residue purified by flash column chromatography (SiO2, DCM/MeOH)
  5. customThe solid obtained
  6. customwas recrystallised from DCM

Sources & evidence

ORD record
ord-e550510e51714b96b48288f576658201
Source dataset
uspto-grants-2012_11
Patent number
US08304425B2

Reaction notes

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