Diisopropylethylamine → HCID 54749368, compound

HRID 1661489Notes

Reaction equation

HRID 1661489 reaction equation
[OH:1][C:2]1[C:3]2[S:23][C:22]([CH3:24])=[N:21][C:4]=2[N:5]([CH3:20])[C:6](=[O:19])[C:7]=1[C:8]([NH:10][CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])=[O:9].C(N(CC)C(C)C)(C)C.OC1C2SC(C)=NC=2N(C)C(=O)C=1C(OCC)=O>O1CCOCC1>[OH:1][C:2]1[C:3]2[S:23][C:22]([CH3:24])=[N:21][C:4]=2[N:5]([CH3:20])[C:6](=[O:19])[C:7]=1[C:8]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=[O:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67428221HCID 67428221, compoundHCID 67983958HCID 67983958, compound

Product 1

HCID 54749368HCID 54749368, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 2-(7-hydroxy-2,4-dimethyl-5-oxo-4,5-dihydrothiazolo[4,5-b]pyridine-6-carboxamido)acetate. N,N-diisopropylethylamine (0.25 g, 2.0 mmol), tert-butyl glycine ester hydrochloride (0.33 g, 2.0 mmol) and ethyl 7-hydroxy-2,4-dimethyl-5-oxo-4,5-dihydrothiazolo[4,5-b]pyridine-6-carboxylate (0.35 g, 1.31 mmol) were heated at 90° C. for 5 hours in 1,4-dioxane (5 mL). The mixture was cooled to room temperature and concentrated to about ¼ of the original volume. Et2O (5 mL) was added, and the resulting suspension was filtered and washed with Et2O to give a solid. This material was washed with cold MeOH (0.5 mL) to give the title compound. MS (ESI) m/z: Calculated; 353.1: Observed; 298.1 (M-tert-butyl+H+). 1H NMR (400 MHz, CDCl3) δ ppm 10.52-10.83 (1H, m), 4.11 (2H, d, J=5.3 Hz), 3.81 (3H, s), 2.83 (3H, s), 1.52 (9H, s)

Workup

  1. concentrationconcentrated to about ¼ of the original volume
  2. additionEt2O (5 mL) was added
  3. filtrationthe resulting suspension was filtered
  4. washwashed with Et2O
  5. customto give a solid
  6. washThis material was washed with cold MeOH (0.5 mL)

Sources & evidence

ORD record
ord-e2b5904fc07342c7bc12dbba920602d2
Source dataset
uspto-grants-2011_10
Patent number
US08030346B2

Reaction notes

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