Triethylamine → HCID 44218581, compound

HRID 1931500Notes

Reaction equation

HRID 1931500 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[CH2:34][C:35](Cl)=[O:36]>C1(C)C=CC=CC=1.O>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:21][C:35](=[O:36])[CH2:34][C:30]4[S:29][CH:33]=[CH:32][CH:31]=4)[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

Product 1

HCID 44218581HCID 44218581, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

(R)—N2-indan-1-yl-quinoline-2,6-diamine (0.10 g, 0.36 mmol), triethylamine (0.055 mL, 0.4 mmol) and 2-thiophenacetyl chloride (0.049 mL, 0.4 mmol) were dissolved in toluene (3.0 mL). The reaction mixture was heated to 50° C. for 10 h. The reaction mixture was diluted with water and extracted with dichloromethane (3×). The combined organic phases were dried on sodium sulfate and evaporated. The crude product was purified by column chromatography (silica gel, heptane ethyl acetate 4:1/2:1/1:1/1:2). The title compound (0.077 g, 53%) was obtained as a yellow solid; MS: m/e=400.6 (M+H+).

Workup

  1. extractionextracted with dichloromethane (3×)
  2. customThe combined organic phases were dried on sodium sulfate
  3. customevaporated
  4. customThe crude product was purified by column chromatography (silica gel, heptane ethyl acetate 4:1/2:1/1:1/1:2)

Sources & evidence

ORD record
ord-b6b97e7d52bc4ab0b5212d98b7033c58
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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