Ammonium Chloride → HCID 178504673, compound

HRID 423705Notes

Reaction equation

HRID 423705 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]#[N:26])[CH2:21][CH2:20]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl-].[NH4+].[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C=O)C>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]4[NH:31][N:30]=[N:29][N:26]=4)[CH2:21][CH2:20]3)=[CH:15][N:16]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86638752HCID 86638752, compound

Product 1

HCID 178504673HCID 178504673, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarbonitrile (241 mg, 0.65 mmol) in DMF (3 mL) was treated with ammonium chloride (52 mg, 0.97 mmol) and sodium azide (63 mg, 0.97 mmol) at room temperature. The mixture was heated at 100° C. for 19 h. After cooling down, the solid was removed by filtration and washed with DMF. The filtrate was concentrated and a small amount of MeOH and CH2Cl2 was added to the residue. After sonication, the resulting precipitate was collected and washed with THF including a small amount of water. 2-[4-(Methylsulfonyl)phenyl]-5-({[1-(1H-tetrazol-5-yl)-4-piperidinyl]methyl}oxy)pyridine was obtained as a light gray solid (170 mg, 60%) after drying in vacuo. 1H NMR (400 MHz, DMSO-d6): δ 8.44 (d, 1H, J=2.9 Hz), 8.28 (d, 2H, J=8.6 Hz), 8.07 (d, 1H, J=8.8 Hz), 7.99 (d, 2H, J=8.6 Hz), 7.55 (dd, 1H, Ja=8.8 Hz, Jb=2.9 Hz), 4.03 (d, 2H, J=6.3 Hz), 3.88 (d, 2H, J=12.7 Hz), 3.25 (s, 3H), 3.13-3.00 (m, 2H), 2.13-2.01 (m, 1H), 1.93-1.84 (m, 2H), 1.47-1.31 (m, 2H); LRMS (ESI), m/z 415 (M+H).

Workup

  1. temperatureAfter cooling down
  2. customthe solid was removed by filtration
  3. washwashed with DMF
  4. concentrationThe filtrate was concentrated
  5. additiona small amount of MeOH and CH2Cl2 was added to the residue
  6. customAfter sonication
  7. customthe resulting precipitate was collected
  8. washwashed with THF including a small amount of water

Sources & evidence

ORD record
ord-bbe1112811754be7bfd2bb03e46e28bb
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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