HCID 24959329, compound → HCID 24959330, compound

HRID 2381822Notes

Reaction equation

HRID 2381822 reaction equation
C(OC[N:10]1[N:14]=[N:13][C:12]([C:15]2[S:16][C:17]([C:21]([NH:23][CH2:24][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[O:22])=[C:18]([CH3:20])[N:19]=2)=[N:11]1)C1C=CC=CC=1>CO.Cl>[CH3:20][C:18]1[N:19]=[C:15]([C:12]2[N:13]=[N:14][NH:10][N:11]=2)[S:16][C:17]=1[C:21]([NH:23][CH2:24][C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)=[O:22]

Participants

4

Reactant 1

HCID 24959329HCID 24959329, compound

Product 1

HCID 24959330HCID 24959330, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2-(2-(benzyloxymethyl)-2H-tetrazol-5-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide (2.80 g, 6.65 mmol) in a mixture of methanol (20 mL) and hydrochloric acid (1 mL) was refluxed for 17 hours. The reaction mixture was cooled to ambient temperature and methanol was removed in vacuo. The residue was diluted with water (20 mL), basified with 1% sodium hydroxide and extracted with ethyl acetate (7 mL). The aqueous layer was cooled to 0° C. and acidified with 1% hydrochloric acid. The white solid obtained was filtered and dried in air to afford the title compound in 80% yield (1.60 g): mp>200° C. (decomposition); 1H NMR (300 MHz, DMSO-d6) δ 9.08 (t, J=5.8 Hz, 1H), 8.59 (br s, 1H), 8.51 (br s, 1H), 7.89-7.82 (m, 1H), 7.52-7.42 (m, 1H), 5.04 (br s, 1H), 4.47 (d, J=5.8 Hz, 2H), 2.64 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.2, 156.6, 152.6, 147.9, 147.4, 137.4, 135.7, 128.2, 124.6, 41.1, 17.4; MS (ES−) m/z 300.3 (M−1).

Workup

  1. temperaturewas refluxed for 17 hours
  2. custommethanol was removed in vacuo
  3. additionThe residue was diluted with water (20 mL)
  4. extractionextracted with ethyl acetate (7 mL)
  5. temperatureThe aqueous layer was cooled to 0° C.
  6. customThe white solid obtained
  7. filtrationwas filtered
  8. customdried in air

Sources & evidence

ORD record
ord-c898a29e5bc64a139667e13aed49f63a
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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