Triethylamine → HCID 57758308, compound

HRID 229629Notes

Reaction equation

HRID 229629 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[C:9]([C:11]([NH:13][CH3:14])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[C:24]([C:28]1[CH:33]=[CH:32][N:31]=[C:30]([NH:34][C:35](=O)[O:36]C2C=CC=CC=2)[CH:29]=1)([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:35]([NH:34][C:30]4[CH:29]=[C:28]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:33]=[CH:32][N:31]=4)=[O:36])=[CH:17][CH:16]=3)[C:9]([C:11]([NH:13][CH3:14])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57758139HCID 57758139, compoundHCID 66589372HCID 66589372, compound

Product 1

HCID 57758308HCID 57758308, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of DMF (1 mL) was added Intermediate X (50 mg, 0.18 mmol) followed by phenyl (4-tert-butylpyridin-2-yl)carbamate (48 mg, 0.18 mmol) and triethylamine (25 μL, 0.18 mmol). The reaction was stirred at rt overnight, concentrated to dryness, and purified by HPLC to afford 22 mg of the above compound (0.04 mmol, yield 26%). 1H-NMR (DMSO-d6) δ 10.9 (s, 1H), 9.48 (s, 1H), 8.17 (d, J=5.4 Hz, 1H), 8.06 (s, 1H), 7.88 (s, 1H), 7.02 (d, J=5.0 Hz, 1H), 7.61 to 7.54 (m, 3H), 7.29 (d, J=8.3 Hz, 2H), 7.04 (dd, J=5.5, 1.6 Hz, 1H), 2.61 (d, J=4.7 Hz, 3H), 1.25 (s, 9H); MS [M+H]+=459.2; LCMS RT=2.49.

Workup

  1. concentrationconcentrated to dryness
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-41a27782cb2e41bbad6f654818fa6a1f
Source dataset
uspto-grants-2009_07
Patent number
US07563791B2

Reaction notes

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