Ammonia → HCID 178511880, compound

HRID 1922350Notes

Reaction equation

HRID 1922350 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7](=[O:19])[CH2:6][CH2:5]2.I.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](SC)=[NH:27].N>C(O)C.CO.C(Cl)Cl>[O:19]=[C:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:26]([C:22]3[S:21][CH:25]=[CH:24][CH:23]=3)=[NH:27])[CH:3]=2)[N:8]1[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 533921826-amino-1-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroquinolin-2(1H)-oneHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178511880HCID 178511880, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 6-amino-1-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one (165 mg, 0.636 mmol) in 5 mL of ethanol was treated with methyl thiophene-2-carbimidothioate hydroiodide (363 mg, 1.27 mmol) and stirred for 18 hours at room temperature. The mixture was partitioned between CH2Cl2 (50 mL) and saturated sodium bicarbonate (10 mL). The aqueous layer was extracted with an additional 20 mL CH2Cl2. The combined organic layers were dried over sodium sulfate and concentrated to give a yellow residue which was subjected to flash chromatography on a Biotage system using 5-10% 2M NH3 in MeOH/CH2Cl2 to give a yellow solid. Yield: 157 mg of yellow oil (68%). 1H NMR (CDCl3) δ: 7.44 (d, J=5.4 Hz, 1H), 7.41 (d, J=3.3 Hz, 1H), 7.09 (t, J=4.2 Hz, 1H), 7.06 (d, J=8.4 Hz, 1H), 6.88 (d, J=2.1 Hz, 1H), 6.84 (d, J=4.2 Hz, 1H), 4.86 (br s, 2H), 4.12-4.06 (m, 2H), 2.88-2.83 (m, 2H), 2.75-2.70 (m, 2H), 2.65-2.60 (m, 6H), 1.82-1.78 (m, 4H). MS (ESI): 369.2 (M+1). ESI-HRMS calculated for C20H25N4SO (MH+): 369.1743, Observed: 369.1731.

Workup

  1. customThe mixture was partitioned between CH2Cl2 (50 mL) and saturated sodium bicarbonate (10 mL)
  2. extractionThe aqueous layer was extracted with an additional 20 mL CH2Cl2
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a yellow residue which
  6. customto give a yellow solid

Sources & evidence

ORD record
ord-50bf4319a0fa44a09cb54ee6668f3aa2
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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