Dimethylformamide → HCID 69673423, compound

HRID 1527619Notes

Reaction equation

HRID 1527619 reaction equation
CN(C=O)C.[CH:6]([CH:8]([C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][NH2:10])=[CH2:7].Cl[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][N:21]=1.C(N(CC)CC)C>O>[CH:6]([CH:8]([C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][NH:10][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][N:21]=1)=[CH2:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 788644-ChloroquinazolineHCID 69673702HCID 69673702, compound

Product 1

HCID 69673423HCID 69673423, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To 15 ml of DMF were added 550 mg of 2-vinyl-4-phenyl-3-butynylamine, 500 mg of 4-chloroquinazoline, and 636 μl of triethylamine, and the mixture was stirred at 80° C. for 5 hours. After cooling the reaction mixture, 20 ml of water was added and two extractions were conducted with 50 ml of ethyl acetate. After being washed twice with 50 ml of saturated brine, the organic layer was dried over sodium sulfate. After filtering the sodium sulfate, the organic layer was concentrated and purified by means of flash chromatography (Isolera™ manufactured by Biotage AB) to give 750 mg of the end product.

Workup

  1. additionwas added
  2. extractiontwo extractions
  3. washAfter being washed twice with 50 ml of saturated brine
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationAfter filtering the sodium sulfate
  6. concentrationthe organic layer was concentrated
  7. custompurified by means of flash chromatography (Isolera™ manufactured by Biotage AB)

Sources & evidence

ORD record
ord-495996e052e346149cb27d1da708f703
Source dataset
uspto-grants-2015_07
Patent number
US09089139B2

Reaction notes

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