Acrylic Acid → HCID 5328419, compound

HRID 1698974Notes

Reaction equation

HRID 1698974 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[C:14]4C=CC=C[C:13]=4[S:12][C:11]=13)[N:8]=[CH:7][N:6]=[C:5]2[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[CH:21]=1.C(O)(=O)C=C.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[NH2:1][C:2]1[C:11]2[S:12][C:4]3[C:5]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[CH:21]=4)=[N:6][CH:7]=[N:8][C:9]=3[C:10]=2[CH:14]=[CH:13][CH:3]=1

Participants

6

Reactant 4

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68468203HCID 68468203, compound

Product 1

HCID 5328419HCID 5328419, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6-amino-4-[(3-bromophenyl)amino]benzothieno-quinazoline (130 mg, 0.35 mmol), acrylic acid (0.05 mL, 0.73 mmol), and triethylamine (0.1 mL, 0.72 mmol) in DMF (3 mL) stirred under N2 at 0° C. was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (144 mg, 0.75 mmol). The reaction gradually warmed up to 25° C. and was quenched with water after 20 hours. The formed yellow solid was collected and purified by sonication with acetone to give the desired product (40 mg, 27%), mp 216.4-217.2° C.

Workup

  1. customThe reaction
  2. customwas quenched with water after 20 hours
  3. customThe formed yellow solid was collected
  4. custompurified by sonication with acetone

Sources & evidence

ORD record
ord-827324f3914f4176ad3d83d25c60e790
Source dataset
uspto-grants-2002_02
Patent number
US06344459B1

Reaction notes

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