Dimethylamine → HCID 66646483, compound

HRID 1893989Notes

Reaction equation

HRID 1893989 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]([NH:16][CH3:17])[N:8]=[C:7]2[C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:35])[C:26]2[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][CH:27]=2)[CH:21]=[CH:22][CH:23]=1.C[CH2:37][N:38]=[C:39]=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.CNC>CN(C)C=O.CN(C)C1C=CN=CC=1.O1CCCC1.C(N(CC)CC)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]([NH:16][CH3:17])[N:8]=[C:7]2[C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:35])[C:26]2[CH:34]=[CH:33][C:29]([C:30]([N:38]([CH3:39])[CH3:37])=[O:32])=[CH:28][CH:27]=2)[CH:21]=[CH:22][CH:23]=1

Participants

9

Reactant 4

HCID 674DimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 25002289HCID 25002289, compound

Product 1

HCID 66646483HCID 66646483, compoundYield 87%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 100 mg of N-[3-(6,7-dimethoxy-2-methylaminoquinazolin-4-yl)phenyl]terephthalamic acid hydrochloride dissolved in 2 mL of dimethylformamide were added 60 mg of WSC, 41 mg of 1-hydroxybenzotriazole, 42 μL of triethylamine, and 10 mg of 4-dimethylaminopyridine, followed by stirring at room temperature for 30 minutes. To the reaction mixture was added 200 μL of a dimethylamine solution in tetrahydrofuran, followed by stirring at room temperature for 15 hours. To the reaction mixture was added 2 mL of tetrahydrofuran, and the reaction mixture was partitioned after addition of a saturated sodium hydrogencarbonate solution. The organic layer was extracted with 10 mL of ethyl acetate, washed with brine, and dried over anhydrous magnesium sulfate. The anhydrous magnesium sulfate was removed by filtration, and the organic layer was concentrated to dryness, and the residue was triturated with a mixed solution consisting of ethyl acetate:n-heptane=1:1. The obtained solid was filtrated, washed with diethyl ether, and dried under aeration to give 85 mg of a target product. Yield: 87%.

Workup

  1. stirringby stirring at room temperature for 15 hours
  2. customthe reaction mixture was partitioned
  3. additionafter addition of a saturated sodium hydrogencarbonate solution
  4. extractionThe organic layer was extracted with 10 mL of ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe anhydrous magnesium sulfate was removed by filtration
  8. concentrationthe organic layer was concentrated to dryness
  9. customthe residue was triturated with a mixed solution
  10. filtrationThe obtained solid was filtrated
  11. washwashed with diethyl ether
  12. customdried under aeration

Sources & evidence

ORD record
ord-0cb0aa7ec3fe4a0085ab7695941ac8e8
Source dataset
uspto-grants-2013_08
Patent number
US08513269B2

Reaction notes

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