Ammonium Chloride → HCID 178481323, compound

HRID 1819306Notes

Reaction equation

HRID 1819306 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[Cl:7][C:8]1[CH:43]=[CH:42][CH:41]=[CH:40][C:9]=1[CH2:10][N:11]1[C:19]2[C:18](=[O:20])[N:17]([CH3:21])[C:16](=[O:22])[N:15]([CH3:23])[C:14]=2[C:13]([C:24]#[N:25])=[C:12]1[N:26]1[CH2:31][CH2:30][CH2:29][C@@H:28]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:27]1.S([O-])(O)(=O)=O.[K+]>CN(C)C=O>[Cl:7][C:8]1[CH:43]=[CH:42][CH:41]=[CH:40][C:9]=1[CH2:10][N:11]1[C:19]2[C:18](=[O:20])[N:17]([CH3:21])[C:16](=[O:22])[N:15]([CH3:23])[C:14]=2[C:13]([C:24]2[NH:25][N:3]=[N:2][N:1]=2)=[C:12]1[N:26]1[CH2:31][CH2:30][CH2:29][C@@H:28]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])[CH2:27]1

Participants

6

Reactant 4

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 516920Potassium bisulfateHCID 57886926tert-Butyl {(3R)-1-[5-(2-chlorobenzyl)-7-cyano-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate

Product 1

HCID 178481323HCID 178481323, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Sodium azide (154 mg) and ammonium chloride (125 mg) were added to a solution of tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-7-cyano-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (250 mg) in N,N-dimethylformamide (4 ml), and the resulting mixture was stirred at 150° C. for 8 hours. Sodium azide (154 mg) and ammonium chloride (125 mg) were further added thereto and stirred for another 6 hours. After the reaction solution was cooled to 25° C., a 10% aqueous potassium hydrogensulfate solution was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by HPLC to obtain the title compound (23 mg) as a white solid.

Workup

  1. stirringstirred for another 6 hours
  2. temperatureAfter the reaction solution was cooled to 25° C.
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by HPLC

Sources & evidence

ORD record
ord-f0dbd14892504a7cae78b6d9d1ba92b9
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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