Hydrochloric Acid → HCID 66965529, compound

HRID 1514964Notes

Reaction equation

HRID 1514964 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([C:16]2[NH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[C:20]([C:25](=[O:37])[NH:26][C:27]2[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=2)[CH:19]=3)=[C:11]([Cl:38])[CH:10]=1)(C)(C)C.Cl>C(Cl)Cl>[ClH:15].[Cl:38][C:11]1[CH:10]=[C:9]([CH2:8][CH2:7][C:6]([OH:39])=[O:5])[CH:14]=[C:13]([Cl:15])[C:12]=1[C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[C:20]([C:25](=[O:37])[NH:26][C:27]1[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]=1)[CH:19]=2

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 66965642HCID 66965642, compound

Product 1

HCID 66965529HCID 66965529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{3,5-dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-indol-2-yl]-phenyl}-propionic acid tert-butyl ester (139 mg, 0.25 mmol) in DCM (1 mL) was added HCl (4M in 1,4-dioxane, 1 mL) and the solution was stirred for 2 h, after which more HCl (4M in 1,4-dioxane, 2 mL) was added. The mixture was stirred for 18 h then the solvent was removed under reduced pressure and the remaining solid was triturated with ether to obtain the title compound as a yellow solid. MS (m/z) 504.1 (M+1); 1H NMR (DMSO-d6, 400 MHz) δ 11.83 (s, 1H), 11.14 (s, broad, 1H), 8.44 (d, J=9.17 Hz, 1H), 8.36 (d, J=8.98 Hz, 1H), 7.97 (dd, J=8.21, 0.88 Hz, 1H) 8.21 (s, 1H), 7.92 (d, J=8.34 Hz, 1H), 7.80 (dd, J=8.40, 1.58 Hz, 1H), 7.76 (td, J=7.71, 1.39 Hz, 1H), 7.69 (d, J=8.34 Hz, 1H), 7.53 (m, 1H) 7.56 (s, 2H), 6.59 (dd, J=1.89, 0.76 Hz, 1H), 2.91 (t, J=7.39 Hz, 2H), 2.63-2.68 (m, 2H).

Workup

  1. stirringThe mixture was stirred for 18 h
  2. customthe solvent was removed under reduced pressure
  3. customthe remaining solid was triturated with ether

Sources & evidence

ORD record
ord-1f0633f2954d48348df59fac9ee74707
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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