Ammonia → HCID 178456218, compound

HRID 1922379Notes

Reaction equation

HRID 1922379 reaction equation
[N:1]1([CH:6]([CH3:19])[CH2:7][N:8]2[C:17]3[C:12](=[CH:13][C:14]([NH2:18])=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.I.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](SC)=[NH:27].N>CCO.CO.C(Cl)Cl>[N:1]1([CH:6]([CH3:19])[CH2:7][N:8]2[C:17]3[C:12](=[CH:13][C:14]([NH:18][C:26]([C:22]4[S:21][CH:25]=[CH:24][CH:23]=4)=[NH:27])=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 59807132HCID 59807132, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178456218HCID 178456218, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 1-(2-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amine (130 mg, 0.50 mmol) in 10 mL EtOH was treated with methyl thiophene-2-carbimidothioate hydroiodide (285 mg, 1.00 mmol) and stirred at room temperature for 3 days. Argon was bubbled through the solution for 20 minutes. The solution was partitioned between CH2Cl2 (100 mL) and saturated sodium carbonate (15 mL). The organic layer was separated and the aqueous layer was extracted with an additional 50 mL CH2Cl2. The combined organic layers were dried over sodium sulfate, filtered and concentrated to give a yellow residue which was subjected to flash chromatography on silica gel using 2.5% MeOH/CH2Cl2 then 5-10% 2M NH3 in MeOH/CH2Cl2. A light orange solid was obtained (100 mg, 54.3%). 1H-NMR (DMSO-d6) δ: 7.67 (d, J=3.6 Hz, 1H), 7.55 (d, J=4.2 Hz, 1H), 7.08-7.05 (m, 1H), 6.56-6.48 (m, 3H), 6.25 (br s, 2H), 3.44 (dd, J=4.5, 14.4 Hz, 1H), 3.33-3.25 (m, 2H), 2.95 (dd, J=8.7, 13.8 Hz, 1H), 2.72-2.58 (m, 7H), 1.86-1.82 (m, 2H), 1.67 (br, 4H), 1.03 (d, J=6.3 Hz, 3H).

Workup

  1. customArgon was bubbled through the solution for 20 minutes
  2. customThe solution was partitioned between CH2Cl2 (100 mL) and saturated sodium carbonate (15 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with an additional 50 mL CH2Cl2
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow residue which
  9. customA light orange solid was obtained (100 mg, 54.3%)

Sources & evidence

ORD record
ord-70ac11f2f5e945b788319f3ef3fd14f2
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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