Triethylamine → HCID 85472070, compound

HRID 871090Notes

Reaction equation

HRID 871090 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:13]3[CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][N:21]=[C:20]5[NH:24][C:25]([CH:27]6[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]6)=[CH:26][C:19]=45)[CH:16]=[CH:17][C:12]=3[N:11]=[CH:10]2)[CH:5]=[N:6][CH:7]=1.FC(F)(F)C([O-])=O.C(N(CC)CC)C.[N:47]([CH3:50])=[C:48]=[O:49]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:13]3[CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][N:21]=[C:20]5[NH:24][C:25]([CH:27]6[CH2:32][CH2:31][N:30]([C:48]([NH:47][CH3:50])=[O:49])[CH2:29][CH2:28]6)=[CH:26][C:19]=45)[CH:16]=[CH:17][C:12]=3[N:11]=[CH:10]2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 84468TrifluoroacetateHCID 85472347HCID 85472347, compound

Product 1

HCID 85472070HCID 85472070, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 12D trifluoroacetate salt (30.0 mg, 0.070 mmol) in N,N-dimethylformamide (0.3 mL) was added triethylamine (0.05 ml, 0.352 mmol) and isocyanatomethane (6.0 mg, 0.106 mmol). The mixture was stirred at room temperature for 1 hour, concentrated and purified by reverse-phase HPLC (Phenomenex Luna C8 AXIA column, 100 Å) eluting with a gradient of 10-95% acetonitrile/0.1% trifluoroacetic acid in water with 10 mM ammonium acetate to afford the title compound. 1H NMR (400 MHz, dimethylsulfoxide-d6) δ 1.51-1.66 (m, 2 H) 1.87-1.98 (m, 2 H) 2.61 (d, J=4.58 Hz, 3 H) 2.74-2.91 (m, 3 H) 4.04 (m, 2 H) 5.66 (s, 2 H) 6.11 (s, 2 H) 7.10 (d, J=4.88 Hz, 1 H) 7.57 (dd, J=8.54, 1.53 Hz, 1 H) 7.61-7.68 (m, 1 H) 7.76-7.83 (m, 2 H) 8.16 (d, J=5.19 Hz, 1 H) 8.42 (s, 1 H) 8.47-8.52 (m, 2 H) 11.32 (s, 1 H). MS (ESI) m/e 484 (M+H)+.

Workup

  1. concentrationconcentrated
  2. custompurified by reverse-phase HPLC (Phenomenex Luna C8 AXIA column, 100 Å)
  3. washeluting with a gradient of 10-95% acetonitrile/0.1% trifluoroacetic acid in water with 10 mM ammonium acetate

Sources & evidence

ORD record
ord-9528410b77e941b78be21f7545af00c0
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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