Triethylamine → HCID 44218109, compound

HRID 1931496Notes

Reaction equation

HRID 1931496 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.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:41][C:42]1[CH:47]=[CH:46][N:45]=[C:44]([Cl:48])[CH:43]=1>C1COCC1.O>[Cl:48][C:44]1[CH:43]=[C:42]([NH:41][C:30]([NH:21][C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[N:12]=[C:11]([NH:10][C@H:1]2[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]2)[CH:20]=[CH:19]3)=[O:32])[CH:47]=[CH:46][N:45]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 844322-Chloropyridin-4-amineHCID 94429TriphosgeneHCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

Product 1

HCID 44218109HCID 44218109, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(R)—N2-indan-1-yl-quinoline-2,6-diamine (100 mg, 0.36 mmol) and triethylamine (55 μL, 0.8 mmol) were dissolved in THF (5 mL). At 0° C. triphosgene (48.5 mg, 0.16 mmol) was added and the reaction mixture stirred for 5 h at reflux. Then at ambient temperature 4-amino-2-chloropyridine (63 mg, 0.36 mmol) and triethylamine (55 μL, 0.8 mmol) were added. After stirring the reaction mixture at 50° C. over night water was added (20 mL) and the mixture extracted with ethyl acetate (3×15 mL). The combined organic phases were dried on sodium sulfate, filtered and evaporated. The residue was subjected to column chromatography (silica gel; methylene chloride, methanol 100:0=>90:10) to yield the title compound (68 mg, 44%) as a yellow solid; MS: (ISP) 431.0 [(M+H)+].

Workup

  1. temperatureat reflux
  2. additionwas added (20 mL)
  3. extractionthe mixture extracted with ethyl acetate (3×15 mL)
  4. customThe combined organic phases were dried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-38a63394beab44538cb17efebaa97700
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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