Water → HCID 57986847, compound

HRID 871950Notes

Reaction equation

HRID 871950 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-560ed33ce8ea4a3cb32716d293b9b6f3
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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