Benzyl isocyanate → HCID 67517289, compound

HRID 919642Notes

Reaction equation

HRID 919642 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C:8]2[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[CH:19][C:9]=23)[CH2:2]1.[N:20]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[C:21]=[O:22].CCN(C(C)C)C(C)C>C1COCC1>[CH2:23]([NH:20][C:21]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C:8]2[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[CH:19][C:9]=23)[CH2:2]1)=[O:22])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 76639Benzyl isocyanateHCID 81531DiisopropylethylamineHCID 67518186HCID 67518186, compound

Product 1

HCID 67517289HCID 67517289, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(piperidin-3-ylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (62 mg, 0.24 mmol, 1.0 eq) and (isocyanatomethyl)benzene (35 mg, 0.26 mmol, 1.1 eq) in THF (2 mL) were added DIPEA (93 mg, 0.72 mmol, 3.0 eq). The mixture was stirred at rt for 3 h and the solvent was removed in vacuo to afford a residue which was purified by prep-HPLC (MeOH/H2O with 0.05% NH3.H2O) to give the title compound as a light brown solid (23 mg, yield: 11%). 1H NMR (400 MHz, CD3OD) δ: 8.32 (s, 1H), 7.15-7.09 (m, 6H), 6.91 (d, J=3.6 Hz, 1H), 4.23-4.20 (m, 3H), 3.87-3.83 (m, 1H), 3.46-3.34 (m, 3H), 2.09-2.05 (m, 1H), 1.81-1.80 (m, 2H), 1.62-1.59 (m, 1H). ESI-MS (M+H)+: 393.20.

Workup

  1. customthe solvent was removed in vacuo
  2. customto afford a residue which
  3. customwas purified by prep-HPLC (MeOH/H2O with 0.05% NH3.H2O)

Sources & evidence

ORD record
ord-c86185a50616411697515bd8dd49336e
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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