Trifluoroacetic acid → HCID 67447163, compound

HRID 1853788Notes

Reaction equation

HRID 1853788 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/[CH:17]=[CH:18]/[CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([NH:26]C(=O)OC(C)(C)C)[CH2:22][CH2:21]1.C(O)(C(F)(F)F)=O>>[NH2:26][CH:23]1[CH2:22][CH2:21][N:20]([CH2:19]/[CH:18]=[CH:17]/[C:4]2[C:5]3[C:6]4[CH:16]=[CH:15][S:14][C:7]=4[C:8](=[O:13])[NH:9][C:10]=3[CH:11]=[CH:12][C:3]=2[O:2][CH3:1])[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86689493HCID 86689493, compound

Product 1

HCID 67447163HCID 67447163, compoundYield 86%

Procedure

Following General Procedure C, (E)-tert-butyl 1-[3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl]piperidin-4-ylcarbamate (40 mg, 0.085 mmol) was reacted with TFA (1 mL) to afford the desired product (15 mg, 86%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.94 (d, J=5.3 Hz, 1H), 7.86 (d, J=5.3 Hz, 1H), 7.34 (d, J=9.1 Hz, 1H), 7.24 (d, J=9.1 Hz, 1H), 7.06 (d, J=16.0 Hz, 1H), 6.14-6.08 (m, 1H), 4.12 (d, J=7.1 Hz, 2H), 3.84 (br s, 2H), 3.55 (br s, 1H), 3.26 (br s, 3H), 2.38 (d, J=13.3 Hz, 2H), 2.12-2.07 (m, 2H), 1.35-1.31 (m, 1H), 0.96-0.90 (m, 1H); ESI MS m/z 370 [C20H23N3O2S+H]+; HPLC 95.6% (AUC), tR=6.78 min.

Sources & evidence

ORD record
ord-bbc4b866d78f4ba2ac4a5f20720a029d
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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