Hydrochloric Acid → HCID 24808477, compound

HRID 222118Notes

Reaction equation

HRID 222118 reaction equation
C(OC(=O)[NH:7][CH2:8][C@@H:9]([NH:17][C:18]([C:20]1[C:32]2[CH2:31][CH2:30][C:29]3[CH:28]=[N:27][CH:26]=[CH:25][C:24]=3[C:23]=2[N:22]([CH2:33][C:34]([F:37])([F:36])[F:35])[CH:21]=1)=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(C)(C)C.Cl.C(OCC)C>O1CCOCC1>[NH2:7][CH2:8][C@@H:9]([NH:17][C:18]([C:20]1[C:32]2[CH2:31][CH2:30][C:29]3[CH:28]=[N:27][CH:26]=[CH:25][C:24]=3[C:23]=2[N:22]([CH2:33][C:34]([F:37])([F:36])[F:35])[CH:21]=1)=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 24989972HCID 24989972, compound

Product 1

HCID 24808477HCID 24808477, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl[(2S)-3-phenyl-2-({[1-(2,2,2-trifluoroethyl)-4,5-dihydro-1H-pyrrolo[2,3-f]isoquinolin-3-yl]carbonyl}amino)propyl]carbamate L8 (0.38 mmol) in dry dioxane (20 mL), 4M HCl in dioxane (5 mL) was added. The reaction mixture was stirred at rt overnight. The solvent was removed and the residue dissolved with DCM and washed with aq NaHCO3. The organic layer was dried (Na2SO4) and concentrated. Purification by chromatography on silica gel (eluant: DCM/MeOH 19:1) gave, after trituration with diethylether, the title compound (75% yield). ESI (+) MS: m/z 429 (MH+). 1H-NMR: 4.06-4.18 (m, 1H), 5.32 (q, J=8.98, 2H), 7.18 (m, 1H), 7.48 (d, J=5.24, 1H), 7.57 (s, 1H), 7.71 (d, J=8.41, 1H), 8.38 (d, J=5.24, 1H), 8.40 (s, 1H).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved with DCM
  3. washwashed with aq NaHCO3
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by chromatography on silica gel (eluant: DCM/MeOH 19:1)
  7. customgave

Sources & evidence

ORD record
ord-096e007ffe9a411ab14258a6ee5a4aaf
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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