Sodium Azide → HCID 86656002, compound

HRID 2361514Notes

Reaction equation

HRID 2361514 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][CH2:14][N:15]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[N:34]4[C:35]5[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=5[N:37]=[C:33]4[N:32]=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=O)=O)=CC=1.[N-:42]=[N+:43]=[N-:44].[Na+]>CN(C=O)C>[N:42]([CH2:12][CH2:13][CH2:14][N:15]([C:23]1[CH:24]=[CH:25][C:26]([C:29]2[N:34]3[C:35]4[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=4[N:37]=[C:33]3[N:32]=[CH:31][CH:30]=2)=[CH:27][CH:28]=1)[C:16](=[O:17])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N+:43]=[N-:44]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 59489502HCID 59489502, compound

Product 1

HCID 86656002HCID 86656002, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-((4-(benzo[4,5]imidazo[1,2-a]pyrimidin-4-yl)phenyl)(tert-butoxycarbonyl)amino)propyl 4-methylbenzenesulfonate (130 mg, 0.23 mmol) in DMF (2 mL) was added NaN3 (83 mg, 1.3 mmol). The mixture as stirred at rt for 2 h and concentrated under reduced pressure to remove volatiles. The residue was taken up to DCM (50 mL) and washed with water (2×50 mL) and dried over MgSO4 and concentrated to afford the title compound as a yellow solid. The product was used directly for the next reaction without further purification. MS (ESI) m/z [M+H]+444.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove volatiles
  3. washwashed with water (2×50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dcba392b922e44d4b95ab2c06b59abe6
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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