Ammonia → HCID 178456522, compound

HRID 1922377Notes

Reaction equation

HRID 1922377 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH3:14])[C:7](=[O:20])[CH2:6][CH2:5]2.I.[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27](SC)=[NH:28].N>CCO.C(Cl)Cl.CO.C(Cl)Cl>[O:20]=[C:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:27]([C:23]3[S:22][CH:26]=[CH:25][CH:24]=3)=[NH:28])[CH:3]=2)[N:8]1[CH2:12][CH:13]([N:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1)[CH3:14]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 59807033HCID 59807033, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178456522HCID 178456522, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 6-amino-1-(2-(pyrrolidin-1-yl)propyl)-3,4-dihydroquinolin-2(1H)-one (240 mg, 0.88 mmol) in 10 mL EtOH was treated with methyl thiophene-2-carbimidothioate hydroiodide (501 mg, 1.76 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 saturated sodium carbonate (20 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 which was subjected to flash chromatography on silica gel using 2% MeOH/CH2Cl2 then 5-10% 2M NH3 in MeOH/CH2Cl2. A yellow solid was obtained (200 mg, 59.4%). 1H-NMR (DMSO-d6) δ: 7.71 (d, J=3.6 Hz, 1H), 7.57 (d, J=5.4 Hz, 1H), 7.08-7.06 (m, 2H), 6.72-6.71 (m, 2H), 6.41 (br s, 2H), 4.05 (dd, J=9.0, 13.8 Hz, 1H), 3.83 (dd, J=4.8, 13.8 Hz, 1H), 2.79-2.75 (m, 3H), 2.54-2.47 (m, 6H), 1.63 (br, 4H), 0.87 (d, J=6.3 Hz, 3H).

Workup

  1. customwas bubbled through the solution for 20 minutes
  2. customThe solution was partitioned between CH2Cl2 (100 mL) and saturated sodium carbonate (20 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 which
  9. customA yellow solid was obtained (200 mg, 59.4%)

Sources & evidence

ORD record
ord-0812b8ec3c31448db3c88980c0152025
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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