Hydrochloric Acid → HCID 66965742, compound

HRID 1514968Notes

Reaction equation

HRID 1514968 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12]([C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[C:19]([C:23]3[C:28]([Cl:29])=[CH:27][C:26]([O:30]CC4C=CC(OC)=CC=4)=[CH:25][C:24]=3[Cl:40])[NH:20]2)=[CH:16][CH:15]=1)=[O:13].Cl>C(Cl)Cl.CO.O1CCOCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12]([C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[C:19]([C:23]3[C:24]([Cl:40])=[CH:25][C:26]([OH:30])=[CH:27][C:28]=3[Cl:29])[NH:20]2)=[CH:16][CH:15]=1)=[O:13]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66965633HCID 66965633, compound

Product 1

HCID 66965742HCID 66965742, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 2-[2,6-dichloro-4-(4-methoxybenzyloxy)-phenyl]-1H-indole-6-carboxylic acid quinolin-2-ylamide (200 mg, 0.352 mmol) in DCM (7.5 mL) and MeOH (2.5 mL) was added 4 M HCl in dioxane (7.5 mL) and the mixture was stirred for 2.5 hr. The reaction was concentrated under reduced pressured and the concentrate partitioned between EtOAc (150 mL) and sat NaHCO3 (30 mL). The organic phase was dried over Na2SO4 and the solvent evaporated. The residue was triturated with DCM to afford the title compound as an orange solid. MS (m/z) 448.1 (M+1); 1H NMR (DMSO-d6, 400 MHz) δ 11.72 (d, J=1.14 Hz, 1H), 11.04 (s, 1H), 10.68 (s, 1H), 8.36-8.43 (m, 2H), 8.18 (s, 1H), 7.96 (d, J=8.08 Hz, 1H), 7.89 (d, J=8.34 Hz, 1H), 7.79 (dd, J=8.34, 1.26 Hz, 1H), 7.74 (dd, J=15.35, 1.20 Hz, 1H), 7.66 (d, J=8.34 Hz, 1H), 7.52 (t, J=7.52 Hz, 1H), 7.02 (s, 2H), 6.53 (d, J=1.77 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressured
  2. customthe concentrate partitioned between EtOAc (150 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent evaporated
  5. customThe residue was triturated with DCM

Sources & evidence

ORD record
ord-055114269a6e4b45bc6dd6aeae603f79
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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