1-Hydroxybenzotriazole → HCID 58585832, compound

HRID 1297636Notes

Reaction equation

HRID 1297636 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([OH:14])=O)=[C:5]2[O:15][CH3:16].Cl.[NH2:18][CH2:19][C:20](=[O:22])[CH3:21].C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[O:22]=[C:20]([CH3:21])[CH2:19][NH:18][C:12]([C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[O:15][CH3:16])=[CH:3][C:2]([I:1])=[CH:11][CH:10]=2)=[O:14]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 30840252-Propanone, 1-amino-, hydrochlorideHCID 585858316-Iodo-4-methoxy-quinoline-3-carboxylic acid

Product 1

HCID 58585832HCID 58585832, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To the mixture of 6-iodo-4-methoxy-quinoline-3-carboxylic acid (example 1b) (4 g, 12.2 mmol), 1-amino-propan-2-one hydrochloride (3.94 g, 36.5 mmol), HOBt (1.97 g, 14.6 mmol) and DIEA (diisopropylethylamine) (8.5 mL, 48.8 mmol) in DMF (N,N-dimethylformamide) (100 mL) was slowly added the solution of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (5.5 g, 14.6 mmol) in DMF (10 mL). After stirring at room temperature for 12 hours, the product was extracted with methylene chloride (2×300 mL). The combined organic layers were successively washed with a saturated aqueous sodium bicarbonate solution (3×150 mL) and water (3×150 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0-10% MeOH in methylene chloride) afforded 6-iodo-4-methoxy-quinoline-3-carboxylic acid (2-oxo-propyl)-amide (1.63 g, 33%) as a yellow solid. LC-MS m/e 385 (MH+).

Workup

  1. extractionthe product was extracted with methylene chloride (2×300 mL)
  2. washThe combined organic layers were successively washed with a saturated aqueous sodium bicarbonate solution (3×150 mL) and water (3×150 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb8a6908378f4f15b05c657d51b89f3c
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

Loading…