Trifluoroacetic acid → 3-(6-(5-cyclopentylbenzofuran-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)propanoic acid

HRID 2075154Notes

Reaction equation

HRID 2075154 reaction equation
[CH:1]1([C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([C:14]4[CH:15]=[C:16]5[C:21](=[CH:22][CH:23]=4)[CH2:20][N:19]([CH2:24][CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])[CH2:18][CH2:17]5)=[CH:11][C:10]=3[CH:33]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([C:14]4[CH:15]=[C:16]5[C:21](=[CH:22][CH:23]=4)[CH2:20][N:19]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:18][CH2:17]5)=[CH:11][C:10]=3[CH:33]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59595930Tert-butyl 3-(6-(5-cyclopentylbenzofuran-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)propanoate

Product 1

HCID 167375173-(6-(5-cyclopentylbenzofuran-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)propanoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl 3-(6-(5-cyclopentylbenzofuran-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)propanoate (25 mg, 0.056 mmole) in CH2Cl2 (0.5 mL) was added TFA (0.5 mL). The mixture was stirred at room temperature for 3 hours. Under reduced pressure, solvents and excess of TFA were removed affording a yellow oil which was rinsed with a mixture of CH2Cl2/Hexane (1:4) followed by ether. The solvents were removed under vacuum to give the title compound (19 mg, 90%) [hS1P1 EC50=4170 nM]. 1H NMR (400 MHz, CD3OD) δ 7.82 (m, 2H), 7.47 (s, 1H), 7.40 (d, 1H), 7.30 (d, 1H), 7.20 (d, 1H), 7.19 (s, 1H), 4.54 (br, 2H), 3.69 (br, 2H), 3.60 (dd, 2H), 3.28 (m, 2H), 3.10 (m, 1H), 2.96 (dd, 2H), 2.10 (m, 2H), 1.85 (m, 2H), 1.74 (m, 2H), 1.65 (m, 2H). MS (ESI) m/z: Calculated: 389.2; Observed: 390.20 (M++1).

Workup

  1. customUnder reduced pressure, solvents and excess of TFA were removed
  2. customaffording a yellow oil which
  3. washwas rinsed with a mixture of CH2Cl2/Hexane (1:4)
  4. customThe solvents were removed under vacuum

Sources & evidence

ORD record
ord-9358910ea3d34bf28f2fee5f34477d2a
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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