Ammonium Chloride → HCID 178519310, compound

HRID 555287Notes

Reaction equation

HRID 555287 reaction equation
OC1CC2N([C:10]([C:12]3[CH:24]=[CH:23][C:15]4[N:16]([CH2:19][CH2:20][C:21]#[N:22])[CH:17]=[N:18][C:14]=4[CH:13]=3)=[O:11])C(CC2)C1.[N-:25]=[N+:26]=[N-:27].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH:22]1[C:21]([CH2:20][CH2:19][N:16]2[C:15]3[CH:23]=[CH:24][C:12]([CH:10]=[O:11])=[CH:13][C:14]=3[N:18]=[CH:17]2)=[N:27][N:26]=[N:25]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 669878143-[5-(3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carbonyl)-benzoimidazol-1-yl]-propionitrile

Product 1

HCID 178519310HCID 178519310, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-[5-(3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carbonyl)-benzoimidazol-1-yl]-propionitrile (250 mg, 0.7 mmol) in DMF (5 mL) was added sodium azide (184 mg, 2.83 mmol) and ammonium chloride (152 mg, 2.83 mmol) and heated to 100° C. for 12 h. The solvent was evaporated completely; methanol (20 mL) was added and filtered. The filtrate was concentrated and the residue purified by preparative HPLC to give 36 mg (13%) of 3-hydroxy-8-aza-bicyclo[3.2.1]oct-8-yl)-{1-[2-(1H-tetrazol-5-yl)-ethyl]-1H-benzoimidazol-5-yl}-methanone. MS-ESI m/z 368 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 1.3-2.0 (m, 8H), 3.15 (s, 1H), 3.5 (t, 2H), 3.9-4.0 (m, 2H), 4.6 (br, 1H), 4.75 (t, 2H), 7.4 (dd, 1H), 7.6-7.7 (m, 2H), 8.25 (s, 1H).

Workup

  1. customThe solvent was evaporated completely
  2. additionmethanol (20 mL) was added
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-751fef636b3d4d558503480e2feaee59
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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