Trifluoroacetic acid → HCID 67451004, compound

HRID 1853778Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24]2)=[CH:19][CH:18]=1.C(O)(C(F)(F)F)=O>>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][NH:23][CH2:24]2)=[CH:19][CH:18]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86689489HCID 86689489, compound

Product 1

HCID 67451004HCID 67451004, compoundYield 93.7%

Procedure

Following General Procedure C, tert-Butyl 7-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (260 mg, 0.53 mmol) was reacted with TFA (5 mL) afford the desired product (180 mg, 20%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.61-7.56 (m, 1H), 7.55 (dd, J=9.0, 3.2 Hz, 1H), 7.44 (d, J=7.8 Hz, 1H), 7.41-7.36 (m, 1H), 7.22 (d, J=7.8 Hz, 1H), 7.16 (s, 1H), 6.13 (d, J=5.4 Hz, 1H), 4.42 (s, 2H), 3.73 (s, 3H), 3.68-3.54 (m, 2H), 3.29-3.20 (m, 2H).

Sources & evidence

ORD record: ord-c84b6a64cc77448a9e81d24dcebcfefd
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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