tert-Butyl isocyanate → HCID 59735798, compound

HRID 552601Notes

Reaction equation

HRID 552601 reaction equation
[C:1]([N:5]=[C:6]=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([CH:29]=[C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:31]=1)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][N:23]=1)=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[CH2:33]([O:32][C:30]1[CH:29]=[C:18]([CH:17]=[C:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:31]=1)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:24][N:23]=1)=[O:20])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanate2×HCID 23072935HCID 23072935, compound

Product 1

HCID 59735798HCID 59735798, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl isocyanate (51 mg) in THF (5 ml) was treated with 2-[(3,5-dibenzyloxybenzoyl)amino]-5-aminopyridine (212 mg), and stirred at ambient temperature for 24 hours. More tert-butyl isocyanate (0.34 ml) added, and stirring continued at ambient temperature for a further 4 days. Volatile material was removed by evaporation and the residue was triturated under methanol to give the title compound (159 mg) as a solid, 1H NMR δ (d6-DMSO): 1.30 (s, 9H), 5.18 (s, 4H), 6.09 (s, 1H), 6.85 (s, 1H), 7.32 to 7.50 (m, 12H), 7.78 (dd, 1H), 8.04 (d, 1H), 8.38 (s, 1H), 8.44 (s, 1H), 10.65 (s, 1H). MS ES+ 525.61 (M+H)+.

Workup

  1. stirringstirring
  2. waitcontinued at ambient temperature for a further 4 days
  3. customVolatile material was removed by evaporation
  4. customthe residue was triturated under methanol

Sources & evidence

ORD record
ord-9b10c2c420ae4a1babd25966f6549a79
Source dataset
uspto-grants-2011_05
Patent number
US07951830B2

Reaction notes

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