Water → HCID 57986847, compound

HRID 1516531Notes

Reaction equation

HRID 1516531 reaction equation
Cl.[N:2]1([C:7]2[CH:25]=[CH:24][C:10]([O:11][CH2:12][C:13]3[N:14]=[C:15]([CH:18]4[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]4)[S:16][CH:17]=3)=[CH:9][CH:8]=2)[CH:6]=[N:5][N:4]=[N:3]1.ClC1N=[CH:31][CH:30]=[CH:29][N:28]=1.[C:33]([O-])(O)=O.[Na+].O.C[N:40]([CH:42]=O)[CH3:41]>>[CH2:31]([C:30]1[CH:41]=[N:40][C:42]([N:20]2[CH2:21][CH2:22][CH2:23][CH:18]([C:15]3[S:16][CH:17]=[C:13]([CH2:12][O:11][C:10]4[CH:9]=[CH:8][C:7]([N:2]5[CH:6]=[N:5][N:4]=[N:3]5)=[CH:25][CH:24]=4)[N:14]=3)[CH2:19]2)=[N:28][CH:29]=1)[CH3:33]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 744042-ChloropyrimidineHCID 516892Sodium BicarbonateHCID 68663147HCID 68663147, compound

Product 1

HCID 57986847HCID 57986847, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 3-[4-(4-Tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidine hydrochloride (150 mg, 0.407 mmol), 2-chloropyrimidine (0.074 mL, 2.0 eq.) and NaHCO3 (171 mg, 2.03 mmol) in DMF (5 mL) was heated at 90° C. for 4 hours. Water was added and the solution was extracted with ethyl acetate, separated, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (50:50 EtOAc/hexanes) to afford the desired product. 1H NMR (CDCl3): δ 8.91 (1H, s), 8.19 (2H, s), 7.63 (2H, m), 7.26 (1H, s), 7.17 (2H, m), 5.25 (2H, s), 4.97 (1H, m), 4.62 (1H, m), 3.25 (2H, m), 3.07 (1H, m), 2.46 (2H, q), 2.28 (1H, m), 1.88 (2H, m), 1.68 (1H, m), 1.20 (3H, t).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. customseparated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (50:50 EtOAc/hexanes)

Sources & evidence

ORD record
ord-8f976096f8394552923bfa6f4c7083a4
Source dataset
uspto-grants-2012_07
Patent number
US08227495B2

Reaction notes

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