Hydrochloric Acid → HCID 71666010, compound

HRID 508650Notes

Reaction equation

HRID 508650 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C:9]2[C:22]3[C:23]4=[C:24]5[C:19](=[CH:20][CH:21]=3)[CH:18]=[CH:17][CH:16]=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)OC(=O)[C:4]=1[C:26]([O:28][CH3:29])=[O:27].[C:30]1([N:36]2[CH:44]=[C:43]3[C:38]([CH2:39][CH2:40][CH2:41][C:42]3=O)=[N:37]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[OH-].[K+].Cl>CN(C=O)C>[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C:9]2[C:22]3[C:23]4=[C:24]5[C:19](=[CH:20][CH:21]=3)[CH:18]=[CH:17][CH:16]=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)[C:41]2[CH2:40][CH2:39][C:38]3[C:43](=[CH:44][N:36]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:37]=3)[C:42]=2[C:4]=1[C:26]([O:28][CH3:29])=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13792528HCID 13792528, compoundHCID 89724920HCID 89724920, compound

Product 1

HCID 71666010HCID 71666010, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 4-(methylthio)-2-oxo-6-(pyren-1-yl)-2H-pyran-3-carboxylate (400 mg, 1 mmol), 2-phenyl-6,7-dihydro-2H-indazol-4(5H)-one (212 mg, 1 mmol) and powdered KOH (84 mg, 1.5 mmol) in dry DMF (5 mL) was stirred at 25° C. for 8 hr. At the end the reaction mixture was poured into ice water with vigorous stirring and finally neutralized with dilute HCl. The solid thus obtained was filtered and purified on a neutral alumina column using 15% chloroform in hexane as eluent to yield 58% of methyl 8-(methylthio)-2-phenyl-6-(pyren-1-yl)-4,5-dihydro-2H-benzo[e]indazole-9-carboxylate. Yellow solid; mp-174-176° C.; 1H NMR (300 MHz, CDCl3) δ 2.49 (s, 3H, CH3), 2.60-2.67 (m, 2H, CH2), 2.71-2.77 (m, 2H, CH2), 4.08 (s, 3H, OCH3), 7.27-7.36 (m, 2H, ArH), 7.47 (t, J1=8.28 Hz, J2=7.50 Hz, 2H, ArH), 7.65-7.72 (m, 2H, ArH), 7.73-7.81 (m, 1H, ArH), 7.90 (d, J=7.77 Hz, 1H, ArH), 7.99-8.09 (m, 3H, ArH), 8.14 (s, 2H, ArH), 8.18-8.29 (m, 3H, ArH); MS (ESI) m/z551 (M++1).

Workup

  1. stirringwith vigorous stirring
  2. customThe solid thus obtained
  3. filtrationwas filtered
  4. custompurified on a neutral alumina column

Sources & evidence

ORD record
ord-b1d67b5765f4446ca541faa29788e60c
Source dataset
uspto-grants-2015_08
Patent number
US09096539B2

Reaction notes

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