HCID 57695530, compound → HCID 135987529, compound

HRID 2079855Notes

Reaction equation

HRID 2079855 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([C:23]2[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:24]=2[O:32][CH3:33])=[CH:11][C:10]=1[C:34]1[N:38]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[N:37]=[N:36][N:35]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH:29]([C:27]1[CH:26]=[CH:25][C:24]([O:32][CH3:33])=[C:23]([C:12]2[C:13]([OH:15])=[CH:14][C:9]([OH:8])=[C:10]([C:34]3[N:38]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[N:37]=[N:36][N:35]=3)[CH:11]=2)[CH:28]=1)([CH3:31])[CH3:30]

Participants

5

Reactant 2

HCID 57695530HCID 57695530, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 135987529HCID 135987529, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

5% Pd/C was wetted carefully with methanol under N2, then a solution of 5-(4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-yl)-1-(3-methoxy-propyl)-1H-tetrazole (100 mg, 0.17 mmol) in methanol (5 ml) was added. The reaction system was vacuumed and filled with hydrogen three times, and the reaction was stirred under hydrogen at r.t. overnight. After filtering the catalyst over celite, the filtrate was concentrated to give product 5′-isopropyl-2′-methoxy-5-[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-biphenyl-2,4-diol (49 mg, 71%). M.p.: 174-176° C.; 400 MHz 1H NMR (CDCl3) δ: 10.58 (s, 1H), 7.60 (s, 1H), 7.28 (dd, J=2.0 Hz, 8.4 Hz, 1H), 7.15 (d, J=2.4 Hz, 1H), 7.01 (d, J=8.8 Hz, 1H), 6.81 (s, 1H), 6.62 (s, 1H), 4.73 (t, J=6.8 Hz, 2H), 3.90 (s, 3H), 3.38 (t, J=5.6 Hz, 2H), 3.10 (s, 3H), 2.99-2.87 (m, 1H), 2.28 (pent, J=6.4 Hz, 2H), 1.27 (d, J=7.2 Hz, 6H); LCMS: 399 [M+H].

Workup

  1. filtrationAfter filtering the catalyst over celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-19277dccf0cf4f6494ead5da886ec62d
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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