Triethylamine → HCID 57758308, compound

HRID 2198081Notes

Reaction equation

HRID 2198081 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) δ10.9 (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-1ba06f50da5c43aab420e9944232e8e8
Source dataset
uspto-grants-2012_12
Patent number
US08338595B2

Reaction notes

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