Triethylamine → HCID 16041851, compound

HRID 886775Notes

Reaction equation

HRID 886775 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[N:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][C:54]=2[C:56]([OH:58])=O)[CH:49]=[CH:48][CH:47]=1.[NH2:59][C:60]1[CH:61]=[CH:62][CH:63]=[C:64]2[C:69]=1[N:68]=[CH:67][CH:66]=[CH:65]2>C(Cl)Cl.O>[N:68]1[C:69]2[C:64](=[CH:63][CH:62]=[CH:61][C:60]=2[NH:59][C:56]([C:54]2[CH:53]=[CH:52][CH:51]=[C:50]3[C:55]=2[N:46]=[CH:47][CH:48]=[CH:49]3)=[O:58])[CH:65]=[CH:66][CH:67]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 113598-AminoquinolineHCID 665828-Quinolinecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 16041851HCID 16041851, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (192 mg; 0.43 mmol), 1-hydroxybenzotriazole monohydrate (79 mg; 0.59 mmol) and triethylamine (0.200 ml; 1.44 mmol) are added to a solution of quinoline-8-carboxylic acid (50 mg; 0.29 mmol) dissolved in 5 ml of dry CH2Cl2. After stirring for 30 minutes at ambient temperature, 8-aminoquinoline (84 mg; 0.58 mmol) is added and the mixture is stirred for 4 hours 30 minutes at ambient temperature. Water (10 ml) is added and the product is extracted with CH2Cl2 (3×10 ml). The volume is reduced and the product is purified by silica gel chromatography, eluted with CH2Cl2/CH3OH (0 to 2%, v/v) then the solvent is evaporated under reduced pressure and the fractions containing a high proportion of products are repurified by silica gel chromatography, eluted with CH2Cl2/CH3OH (99.5/0.5; v/v). 24 is obtained after evaporation of the solvent in the form of a white powder (83 mg; 0.28 mmol, yield=96%). NMR-1H (250 MHz, CDCl3) δ, ppm: 15.13 (s, 1H); 9.25 (dd, 3J (H, H)=4.0 Hz, 4J (H, H)=2.0 Hz, 1H); 9.19 (dd, 3J (H, H)=7.5 Hz, 4J (H, H)=1.5 Hz, 1H); 9.00 (m, 2H); 8.32 (dd, 3J (H, H)=8.0 Hz, 4J (H, H)=2.0 Hz, 1H); 8.19 (dd, 3J (H, H)=8.0 Hz, 4J (H, H)=1.5 Hz, 1H); 8.01 (dd, 3J (H, H)=8.0 Hz, 4J (H, H)=1.5 Hz, 1H); 7.74 (dd, 3J (H, H)=7.5 and 8.0 Hz, 1H); 7.60 (m, 3H); 7.48 (dd, 3J (H, H)=4.5 and 8.0 Hz, 1H). NMR-13C (63 MHz, CDCl3) δ, ppm: 164.28; 149.48; 148.57; 145.60; 140.12; 137.59; 136.65; 136.18; 134.02; 132.10; 129.85; 128.41; 128.28; 127.50; 126.63; 121.75; 121.34; 121.12; 118.18. MS (CID, NH3): m/z=300 (MH+). UV/vis [DMSO/20 mM Tris-HCl pH=7.4 containing 150 mM NaCl (8/2, v/v)]: λ nm (ε M−1 cm−1)=261 (13,300, shoulder), 274 (14,800), 294 (12,200).

Workup

  1. stirringthe mixture is stirred for 4 hours 30 minutes at ambient temperature
  2. extractionthe product is extracted with CH2Cl2 (3×10 ml)
  3. customthe product is purified by silica gel chromatography
  4. washeluted with CH2Cl2/CH3OH (0 to 2%, v/v)
  5. customthe solvent is evaporated under reduced pressure
  6. additionthe fractions containing a high proportion of products
  7. customare repurified by silica gel chromatography
  8. washeluted with CH2Cl2/CH3OH (99.5/0.5
  9. custom24 is obtained
  10. customafter evaporation of the solvent in the form of a white powder (83 mg; 0.28 mmol, yield=96%)
  11. additionUV/vis [DMSO/20 mM Tris-HCl pH=7.4 containing 150 mM NaCl (8/2

Sources & evidence

ORD record
ord-47366642d7524da2b54f30ca015ea2a3
Source dataset
uspto-grants-2012_08
Patent number
US08247396B2

Reaction notes

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