Acrylic Acid → HCID 5328419, compound

HRID 394761Notes

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

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. 1H NMR [(CD3)2SO]: δ10.64 (s, 1H, NH), 9.84 (s, 1H, NH), 8.77 (s, 1H, H2), 8.73 (d, J=1.5 Hz, 1H, H6), 8.31 (d, 1H, J=8.8 Hz, H8), 8.20 (s, 1H, H2′), 7.84 (d, J=8.3 Hz, 1H, H6′), 7.67 (dd, J=8.6, 1.7 Hz, 1H, H9), 7.34 (t, J=7.8 Hz, 1H, H5′), 7.28 (d, J=8.1 Hz, 1H, H4′), 6.50 (dd, J=16.9, 10.0 Hz, 1H, ═CH), 6.34 (dd, J=17.1, 1.7 Hz, 1H, ═CH2), 5.83 (dd, J=10, 1.7 Hz, 1H ═CH2).

Workup

customThe reaction
customwas quenched with water after 20 hours
customThe formed yellow solid was collected
custompurified by sonication with acetone

Sources & evidence

ORD record: ord-0d40ff27b9834b9089d970606bdb6bfc
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06602863B1

Reaction notes

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