Potassium Carbonate → HCID 69216293, compound

HRID 272715Notes

Reaction equation

HRID 272715 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[C:31]([O:32][CH3:33])=[CH:30][C:8]2[NH:9][C:10](=[O:29])[C:11]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([O:27][CH3:28])[CH:19]=4)=[CH:14][C:12]=3[NH:13][C:7]=2[CH:6]=1.[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:33][O:32][C:31]1[C:5]([O:4][CH2:3][CH2:2][N:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)=[CH:6][C:7]2[NH:13][C:12]3[CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([O:27][CH3:28])[CH:19]=4)[CH:16]=[CH:17][C:11]=3[C:10](=[O:29])[NH:9][C:8]=2[CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 69218697HCID 69218697, compound

Product 1

HCID 69216293HCID 69216293, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 497 (11 mg, 0.023 mmol), pyrrolidine (3.9 μL, 0.046 mmol), K2CO3 (6.5 mg, 0.046 mmol) and DMF (0.5 mL) was heated overnight at 50° C., cooled to room temperature, and filtered. The filtrate was purified by preparative HPLC to provide 6 mg (51%) of the desired product. MS (ESI) m/e 505 (M+H)+; 1H NMR (500 MHz, DMSO-d6) 9.72 (s, 1H), 8.02 (d, J=8.4 Hz, 1H), 7.78-7.80 (m, 2H), 7.53 (d, J=1.6 Hz, 1H), 7.29-7.35 (m, 3H), 6.78 (s, 1H), 6.73 (s, 1H), 4.18 (t, J=5.0 Hz, 2H), 4.03 (s, 3H), 3.71 (s, 3H), 3.44-3.68 (m, 4H), 3.11-3.17 (m, 2H), 2.00-2.07 (m, 2H), 1.95-1.93 (m, 2H).

Workup

  1. filtrationfiltered
  2. customThe filtrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-c904c668fab5461cacd8067e1fd5a0af
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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