Dimethylformamide → HCID 178480086, compound

HRID 2264276Notes

Reaction equation

HRID 2264276 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]3[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]3)[N:11]=2)=[CH:2]1.CI.[C:26]([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[CH3:26][N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]3[CH2:18][CH2:19][C@H:20]([OH:23])[CH2:21][CH2:22]3)[N:11]=2)=[CH:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178521601HCID 178521601, compound

Product 1

HCID 178480086HCID 178480086, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a flask was added compound 18 (17 mg), methyl iodide (7.8 mg), K2CO3 (10 mg), and DMF (1 mL). The mixture was heated to 50° C. for 2 hrs, then poured into water and extracted with EtOAc. The organic layer was separated, dried with MgSO4, then concentrated and the residue was purified by flash chromatography [DCM:MeOH/9.5:0.5] to afford 14 mg (82%) of the desired product. 1H NMR (300 MHz, CDCl3) δ 8.70 (d, 1 H), 8.40 (d, 1 H), 8.20 (d, 1 H), 7.85 (s, 1 H), 7.20 (dd, 1 H), 6.80 (d, 1 H), 5.00 (m, 1 H), 4.30 (m, 1 H), 3.96 (s, 3 H), 3.70 (m, 1 H), 2.30 (m, 2 H), 2.10 (m, 2 H), 1.70 (br s, 1 H), 1.50 (m, 2 H), 1.35 (m, 2 H). MS (ESI) m/I: 324 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. customthe residue was purified by flash chromatography [DCM:MeOH/9.5:0.5]

Sources & evidence

ORD record
ord-bc8dccf6f1b14baf8643fe55532159b2
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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