Ammonium Chloride → HCID 57986823, compound

HRID 871951Notes

Reaction equation

HRID 871951 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[S:17][CH:18]=[C:19]([CH2:21][O:22][C:23]4[CH:28]=[CH:27][C:26]([N:29]5[CH:33]=[N:32][N:31]=[N:30]5)=[CH:25][CH:24]=4)[N:20]=3)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)([O-])=O.[Cl-].[NH4+]>CCO.C1COCC1.O.[Fe]>[N:29]1([C:26]2[CH:27]=[CH:28][C:23]([O:22][CH2:21][C:19]3[N:20]=[C:16]([CH:13]4[CH2:12][CH2:11][N:10]([C:7]5[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][N:6]=5)[CH2:15][CH2:14]4)[S:17][CH:18]=3)=[CH:24][CH:25]=2)[CH:33]=[N:32][N:31]=[N:30]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 57986820HCID 57986820, compound

Product 1

HCID 57986823HCID 57986823, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 18504229Ethanol tetrahydrofuran waterSolvent

Conditions

Temperature
100 °C

Procedure

5-Nitro-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine (Example 192) (1.07 mmol), ammonium chloride (3 eq.) and iron powdcr (3 eq.) were suspended in EtOH:THF:H2O (40:20:10) and heated at 100° C. for 5 hours. The hot reaction mixture was filtered through a pad of celite and the filtrate was concentrated. The resulting oil was dissolved in DMF and water and extracted with ethylacetate. The organic layer was washed with water, brine and dried over sodium sulfate. The resulting filtrate was concentrated under reduced pressure. Purification using silica gel chromatography (DCM/MeOH 98:2) provided the expected product. 1H NMR (DMSO-d6): δ 9.96 (1H, s), 7.97 (2H, m), 7.90 (2H, m), 7.63 (1H, s), 5.19 (2H, s), 4.44 (2H, m), 3.73 (1H, m), 2.97 (2H, m), 2.20 (2H, m), 1.95 (2H, m).

Workup

  1. filtrationThe hot reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe resulting oil was dissolved in DMF
  4. extractionwater and extracted with ethylacetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationThe resulting filtrate was concentrated under reduced pressure
  8. customPurification

Sources & evidence

ORD record
ord-25b587293da746d5ac29f779323338b9
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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