Psi-697 → 8-(4-chlorobenzyl)-7-hydroxy-2,3-dihydro-1H-9-aza-cyclopenta[a]naphthalene-6-carboxylic Acid

HRID 2375557Notes

Reaction equation

HRID 2375557 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]2[C:16]([OH:17])=[C:15]([C:18]([OH:20])=[O:19])[C:14]3[C:9](=[C:10]4[CH2:24][CH2:23]C[CH2:21][C:11]4=[CH:12][CH:13]=3)[N:8]=2)=[CH:4][CH:3]=1.N1C2C(=CC=C3C=2CCC3)C(=O)C1=O.C(OCC(=O)CC1C=CC(Cl)=CC=1)(=O)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:16]([OH:17])=[C:15]([C:18]([OH:20])=[O:19])[C:14]3[C:9]([N:8]=2)=[C:10]2[CH2:24][CH2:23][CH2:21][C:11]2=[CH:12][CH:13]=3)=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 12004316Psi-697HCID 122224641-(Acetyloxy)-3-(4-chlorophenyl)-2-propanoneHCID 148855691,6,7,8-Tetrahydrocyclopenta[g]indole-2,3-dione

Product 1

HCID 161001998-(4-chlorobenzyl)-7-hydroxy-2,3-dihydro-1H-9-aza-cyclopenta[a]naphthalene-6-carboxylic AcidYield 14%

Procedure

This compound was synthesized by the procedure described above for Compound 1, reacting 1,6,7,8-tetrahydro-1-aza-as-indacene-2,3-dione 10 (0.36 g, 1.92 mmol) with 3-(4-chlorophenyl)-2-oxopropyl acetate 2 (0.54 g, 2.40 mmol). The crude acid was purified as described above for Compound 4 to give pure product Compound 5 as a bright yellow powder (94 mg, 14% yield): 1H NMR (400 MHz, DMSO-D6) δ 2.15 (quint., 2H) 3.05 (t, J=7.3 Hz, 2H) 3.28 (t, J=7.5 Hz, 2H) 4.32 (s, 2H) 7.33 (s, 4H) 7.49 (d, J=8.3 Hz, 1H) 8.36 (d, J=8.1 Hz, 1H); HRMS (ESI+) calcd for C20H17ClNO3 (MH+) 354.0892, found 354.0898.

Workup

  1. customThis compound was synthesized by the procedure
  2. customThe crude acid was purified

Sources & evidence

ORD record
ord-bb4d74f30b1f41f28e5c0daa32ccb44d
Source dataset
uspto-grants-2008_12
Patent number
US07465798B2

Reaction notes

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