Acrylic Acid → HCID 67334224, compound

HRID 1675240Notes

Reaction equation

HRID 1675240 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([NH:27][C:28](=[O:35])[C@@H:29]([NH2:34])[CH2:30][CH:31]([CH3:33])[CH3:32])[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[C:36](O)(=[O:39])[CH:37]=[CH2:38].Cl.CN(C)CCCN=C=NCC.C(=O)(O)[O-].[Na+]>C1COCC1.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([NH:27][C:28](=[O:35])[C@@H:29]([NH:34][C:36](=[O:39])[CH:37]=[CH2:38])[CH2:30][CH:31]([CH3:32])[CH3:33])[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 6581Acrylic AcidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67334330HCID 67334330, compound

Product 1

HCID 67334224HCID 67334224, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

480 mg of (2S)-2-amino-4-methyl-pentanoic acid {4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-quinazolin-6-yl}-amide was dissolved in 10 ml of THF, cooled to 0° C., and the resulting solution was treated with 0.1 ml of acrylic acid, 0.16 ml of pyridine and 376 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride at 0° C. for 1 hour and at room temperature for 2 hours. The resulting solution was treated with saturated sodium bicarbonate, extracted with chloroform, dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure. The resulting residue was subjected to column chromatography (eluent-ethylacetate:methanol=30:1) to obtain the title compound of formula (162 mg, 31%).

Workup

  1. extractionextracted with chloroform
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-152996a494c243a682fbab012f540d24
Source dataset
uspto-grants-2011_08
Patent number
US08003658B2

Reaction notes

Loading…