tert-Butyl isocyanate → HCID 58710066, compound

HRID 2375891Notes

Reaction equation

HRID 2375891 reaction equation
[C:1]1([NH:11][C:12]2[C:13]3[CH:20]=[C:19]([C:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH:26]=4)[NH:18][C:14]=3[N:15]=[CH:16][N:17]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:27]([N:31]=[C:32]=[O:33])([CH3:30])([CH3:29])[CH3:28].C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>CN(C)C=O>[C:27]([NH:31][C:32]([N:24]1[CH2:23][CH:22]=[C:21]([C:19]2[NH:18][C:14]3[N:15]=[CH:16][N:17]=[C:12]([NH:11][C:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)[C:13]=3[CH:20]=2)[CH2:26][CH2:25]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 62412tert-Butyl isocyanateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 58709979HCID 58709979, compound

Product 1

HCID 58710066HCID 58710066, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension containing naphthalen-1-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine (120 mg, 0.35 mmol), tert-butyl isocyanate (35 mg, 0.35 mmol) and N,N-diisopropylethylamine (122 μL, 0.70 mmol) in anhydrous N,N-dimethylformamide (2 mL) was stirred overnight at rt. The reaction mixture was poured into saturated NaHCO3 solution (50 mL) and extracted with EtOAc (3×50 ml). The combined organics were washed with brine (3×50 mL), dried (MgSO4), filtered and concentrated. Flash chromatography (2 to 4% MeOH in DCM) gave the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ=8.13 (1H, s), 8.08-8.02 (2H, m), 7.89 (1H, d, J=8.1 Hz), 7.74-7.71 (1H, m), 7.63-7.54 (3H, m), 6.55 (1H, d, J=8.3 Hz), 6.43 (1H, s), 5.83 (1H, s), 4.04 (2H, s), 3.55 (2H, t, J=5.6 Hz), 2.42 (2H, s), 1.34 (9H, s); MS (ES+): m/z 441.08 [MH+], HPLC: tR=2.59 min (MicromassZQ, polar—5 min).

Workup

  1. extractionextracted with EtOAc (3×50 ml)
  2. washThe combined organics were washed with brine (3×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-15672aae31084f4aa801e4b45ad75daf
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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