Ammonia → HCID 178480392, compound

HRID 1922416Notes

Reaction equation

HRID 1922416 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([N:7]2[C:16]3[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=3)[CH2:10][CH2:9][CH2:8]2)[CH2:3]1.I.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](SC)=[NH:25].N.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(O)C.C(Cl)Cl.CO.C(Cl)Cl>[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([N:7]2[C:16]3[C:11](=[CH:12][C:13]([NH:17][C:24]([C:20]4[S:19][CH:23]=[CH:22][CH:21]=4)=[NH:25])=[CH:14][CH:15]=3)[CH2:10][CH2:9][CH2:8]2)[CH2:3]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 53392449HCID 53392449, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178480392HCID 178480392, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 1-(1-methylpyrrolidin-3-yl)-1,2,3,4-tetrahydroquinolin-6-amine (80 mg, 0.35 mmol) in 8 mL ethanol was treated with methyl thiophene-2-carbimidothioate hydroiodide (197 mg, 0.69 mmol) and stirred overnight at room temperature. The mixture was diluted with CH2Cl2 (10 mL) and argon was bubbled through the solution for 20 minutes. The solution was partitioned between CH2Cl2 (100 mL) and 1N NaOH (20 mL). After extraction, the organic layer was separated, dried over sodium sulfate, filtered and concentrated to give a dark residue which was subjected to flash chromatography on silica gel using 2.5% MeOH/CH2Cl2 then 5% 2M NH3 in MeOH/CH2Cl2. A light brown solid was obtained. This compound was converted to the dihydrochloride salt (95 mg, 65.6%). 1H-NMR (DMSO-d6) δ 7.67 (d, J=3.3 Hz, 1H), 7.55 (d, J=5.1 Hz, 1H), 7.08-7.06 (m, 1H), 6.70 (d, J=8.7 Hz, 1H), 6.55-6.50 (m, 2H), 6.29 (brs, 2H), 4.46-4.37 (m, 1H), 3.21-3.15 (m, 2H), 2.74-2.69 (m, 4H), 2.50-2.43 (m, 2H), 2.25 (s, 3H), 2.15-2.04 (m, 1H), 1.86-1.67 (m, 3H). MS (ESI): 341.2 (M+1). ESI-HRMS calculated for C19H25N4S (MH+): 341.1794, Observed: 341.1788.

Workup

  1. customwas bubbled through the solution for 20 minutes
  2. customThe solution was partitioned between CH2Cl2 (100 mL) and 1N NaOH (20 mL)
  3. extractionAfter extraction
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a dark residue which
  9. customA light brown solid was obtained

Sources & evidence

ORD record
ord-00a9df96fede420db2c6f93f532c5c1c
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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