Dimethylformamide → HCID 44474165, compound

HRID 889605Notes

Reaction equation

HRID 889605 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C=O)C.[CH3:25][O:26][C:27]1[N:32]=[C:31]2[S:33][C:34]([NH2:36])=[N:35][C:30]2=[CH:29][CH:28]=1>S(Cl)(Cl)=O.N1C=CC=CC=1>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[C:8]([NH:36][C:34]2[S:33][C:31]3[C:30]([N:35]=2)=[CH:29][CH:28]=[C:27]([O:26][CH3:25])[N:32]=3)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 28015575-Methoxy[1,3]thiazolo[5,4-b]pyridin-2-amineHCID 117371213-Cyclopentyl-2-(4-nitrophenyl)propionic acid

Product 1

HCID 44474165HCID 44474165, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 24386Thionyl ChlorideSolvent

Procedure

The title B compound, 3-cyclopentyl-2-(4-nitro-phenyl)-propionic acid (7.5 g, 28.5 mmol) is dissolved in 25 mL of thionyl chloride and a drop of DMF and the mixture stirred at RT for 5-6 h. The excess of thionyl chloride is removed under reduced pressure. The residue is then taken up in DCM and added dropwise to a solution of the title E compound in Example 1, 5-methoxy-thiazolo[5,4-b]pyridin-2-ylamine (5.2 g, 28.5 mmol) in 25 mL of pyridine. The reaction mixture is stirred for 5 h before being evaporated to remove the pyridine. The residue is partitioned between ethyl acetate and brine, extracted with ethyl acetate. The combined organic layers are washed with saturated sodium bicarbonate, brine, dried over anhydrous magnesium sulfate, filtered and then reduced to an orange-brown solid. This is then vacuum dried to afford 3-cyclopentyl-N-(5-methoxy-thiazolo[5,4-b]pyridin-2-yl)-2-(4-nitro-phenyl)-propionamide as a foam: 1H NMR (400 MHz, CDCl3) δ 1.0-1.1 (m, 2H), 1.4-1.8 (m, 5H), 1.8-1.9 (m, 2H), 2.1-2.25 (m, 2H), 3.6 (t, 1H, J=7.8), 4.01 (s, 3H), 6.8 (d, 1H, J=8.8), 7.4 (d, 2H, J=8.6), 7.8 (d, 1H, J=8.8 Hz), 8.19 (d, 2H, J=8.6 Hz), 9.3 (s, 1H); LC/MS 427 (M+1).

Workup

  1. customThe excess of thionyl chloride is removed under reduced pressure
  2. custombefore being evaporated
  3. customto remove the pyridine
  4. customThe residue is partitioned between ethyl acetate and brine
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers are washed with saturated sodium bicarbonate, brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customvacuum dried

Sources & evidence

ORD record
ord-974cda1d0e2145588a51f87b10794ace
Source dataset
uspto-grants-2012_08
Patent number
US08252931B2

Reaction notes

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