Methanol → HCID 68865469, compound

HRID 1726001Notes

Reaction equation

HRID 1726001 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:16]2[CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:22])[C:15]2=[CH:14][CH:13]=1)(=[O:10])=[O:9].[CH3:28]O>[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([O:22][CH3:28])[C:15]2=[CH:14][CH:13]=1)(=[O:10])=[O:9].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:15]2=[CH:14][CH:13]=1)(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 887MethanolHCID 68864572HCID 68864572, compound

Product 2

HCID 68865469HCID 68865469, compoundHCID 68866512HCID 68866512, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of Example 510F (3.47 g, 8.87 mmol) in 100:1 methanol/concentrated HCl (152 mL) was added to 10% Pd/C (700 mg). The resulting suspension was reacted under 60 psi H2 at 50° C. for 16 hours and filtered. The filtrate was concentrated and purified by flash chromatography to provide Example 510G (methyl 2-{[(2-fluorophenyl)sulfonyl]amino}-5-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulene-1-carboxylate) (1.16 g, 32%) and Example 510H (methyl 2-{[(2-fluorophenyl)sulfonyl]amino}-6,7,8,9-tetrahydro-5H-benzo[7]annulene-1-carboxylate) (1.05 g, 31%). Example 510G: MS (ESI(+)) m/e 408 (M+H)+, 425 (M+NH4)+; MS (ESI(−)) m/e 406 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.00 (br s, 1H), 7.69 (m, 2H), 7.42 (t, 1H), 7.31 (t, 1H), 7.28 (d, 1H), 7.00 (d, 1H), 4.37 (d, 1H), 3.65 (s, 3H), 3.21 (s, 3H), 2.70 (m, 1H), 2.49 (m, 1H), 1.61 (m, 2H), 1.59 (m, 3H), 1.37 (m, 1H). Example 510H: MS (ESI(+)) m/e 378 (M+H)+, 395 (M+NH4)+, 400 (M+Na)+; MS (ESI(−)) m/e 376 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.86 (br s, 1H), 7.61 (m, 2H), 7.35 (dd, 1H), 7.24 (td, 1H), 7.06 (d, 1H), 6.81 (d, 1H), 3.58 (s, 3H), 2.67 (t, 2H), 2.50 (m, 2H), 1.65 (m, 2H), 1.42 (m, 2H).

Workup

  1. customThe resulting suspension was reacted under 60 psi H2 at 50° C. for 16 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-20892dcbd3494e4ab55219d0c81d4aff
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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