Hydrochloric Acid → HCID 68517078, compound

HRID 1873679Notes

Reaction equation

HRID 1873679 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[C@H:10]([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)[CH2:9]1)=O)(C)(C)C.[ClH:34].O1CCOCC1>C(Cl)Cl>[ClH:34].[NH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([C@@H:11]2[CH2:12][NH:8][CH2:9][C@H:10]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:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59404392HCID 59404392, compound

Product 1

HCID 68517078HCID 68517078, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.205 g, 0.46 mmol) in DCM (10 mL) was added HCl 4M in dioxane (1.15 mL, 4.6 mmol) under N2. The mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure and the residue washed with DCM. Re-crystallization from EtOH gave 1-[(3R,4R)-4-(1H-Indol-3-yl)-pyrrolidin-3-yl]-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline HCl salt as a white solid. M.p.=dec.>70° C.; 1H NMR (400 MHz, DMSO-d6) δ: 10.95 (s, 1H), 9.24 (s, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.39 (d, J=8.0 Hz, 1H), 7.32-7.26 (m, 3H), 7.05 (t, J=7.6 Hz, 1H), 6.94 (t, J=7.6 Hz, 1H), 6.87 (t, J=7.6 Hz, 1H), 6.80 (d, J=7.2 Hz, 1H), 4.03 (m, 4H), 3.85 (br s, 1H), 3.52-3.35 (m, 3H), 2.85 (t, J=6.0 Hz, 2H), 2.05 (m, 2H). LCMS: m/e 342.17 [M+H].

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe residue washed with DCM

Sources & evidence

ORD record
ord-73b1044a7223450b968cba5fbd916b2e
Source dataset
uspto-grants-2012_11
Patent number
US08304425B2

Reaction notes

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