HCID 19017715, compound → HCID 178448917, compound

HRID 1728345Notes

Reaction equation

HRID 1728345 reaction equation
[CH2:1]([N:5]=[C:6]1[S:10][CH:9]=[N:8][C:7]1([C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]2[N:28](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:27]=[N:26][N:25]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.O1CCCC1.O>[CH2:1]([N:5]=[C:6]1[S:10][CH:9]=[N:8][C:7]1([C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]2[NH:25][N:26]=[N:27][N:28]=2)=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 19017715HCID 19017715, compound

Product 1

HCID 178448917HCID 178448917, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

5-Butylimino-4,5-dihydro-4-ethoxycarbonyl-4-[[2'-(N-triphenylmethyl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl]thiazole, the compound resulting from Example 2A (B), (170 mg, 0.241 mmol) in 15:15:1 (v/v/v) acetic acid/tetrahydrofuran/water (4 mL) was heated at reflux for 90 minutes. The solvent was evaporated under reduced pressure, and toluene was added and evaporated. Chromatography of the residue on silica gel eluting with 2-6% methanol in chloroform afforded 33.6 mg (30%) of the desired product as a yellow foam solid. TLC (10% methanol/90% chloroform) Rf =0.33. 1H NMR (CDCl3, 300 MHz) d 0.88 (t, 3H), 1.23 (t, 3H), 1.10-1.65 (envelope, 4H), 3.61 (d, 1H), 3.75 (dt, 2H), 3.81 (d, 1H), 4.08-4.32 (m, 2H), 7.08 (d, 2H), 7.27 (d, 2H), 7.38 (dd, 1 H), 7.50-7.63 (m, 2H), 7.75 (s, 1H), 8.20 (dd, 1H). MS (DCl/NH3) m/e 463 (M+H)+. Anal calcd for C24H26N6O2S.0.25 H2O: C, 61.72; H, 5.72; N, 17.99. Found: C, 61.89; H, 5.32; N, 17.76.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 90 minutes
  3. customThe solvent was evaporated under reduced pressure, and toluene
  4. additionwas added
  5. customevaporated

Sources & evidence

ORD record
ord-ecb4f942b5c54e8087135abdd6bad80f
Source dataset
uspto-grants-1994_07
Patent number
US05326776

Reaction notes

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