Dimethylformamide → HCID 22338310, compound

HRID 585901Notes

Reaction equation

HRID 585901 reaction equation
[NH:1]1CCC[CH2:3][CH2:2]1.C1C2C(COC(=O)NC(N3C4[C:30](=[CH:31][CH:32]=[C:33]5[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:34]5=4)[CH:29]=[N:28]3)(C)C)C3C(=CC=CC=3)C=2C=CC=1.C([O-])(O)=O.[Na+].C[N:49]([CH:51]=O)[CH3:50]>>[CH3:41][O:40][C:38]1[CH:37]=[CH:36][C:34]2[C:33]([CH:39]=1)=[CH:32][CH:31]=[C:30]1[C:50]=2[N:49]([CH2:51][CH:2]([NH2:1])[CH3:3])[N:28]=[CH:29]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 69752497HCID 69752497, compound

Product 1

HCID 22338310HCID 22338310, compoundYield 64%

Conditions

Temperature
23 °C

Procedure

A solution of piperidine in DMF (1:4, 5 mL) was added to the product of Step C (0.1 g, 0.2 mmol) and the solution was stirred for 5 minutes at 23° C., poured into aqueous NaHCO3, and extracted with ethyl acetate (2×20 mL). The combined extracts were dried (MgSO4) and concentrated to a residue, which was purified by chromatography (silica, gradient, 3 to 10% methanol in dichloromethane) to give an oil (0.035 g, 64%): 1H NMR (CDCl3) δ 8.27 (d, J=9.0 Hz, 1H), 8.01 (s, 1H), 7.64 (d, J=9.0 Hz, 1H), 7.41 (d, J=8.4 Hz, 1H), 7.34 (d, J=2.4 Hz, 1H), 7.26 (m, 1H), 4.76 (dd, J=14.4, 4.8 Hz, 1H), 4.63 (dd, J=14.4, 8.4 Hz, 1H), 3.96 (s, 3H), 3.67 (m, 1H), 1.25 (d, J=6.0 Hz, 3H); MS m/z 256 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated to a residue, which
  4. customwas purified by chromatography (silica, gradient, 3 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8eb20467188e488fbbb8c01ae490fa2f
Source dataset
uspto-grants-2005_08
Patent number
US06933392B2

Reaction notes

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