Hydrazine hydrate (1:1) → HCID 88158463, compound

HRID 650970Notes

Reaction equation

HRID 650970 reaction equation
[Br:1][C:2]([Br:29])=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][C@H:13]([CH2:15][N:16]3C(=O)C4[C:18](=CC=CC=4)[C:17]3=[O:26])[O:12][C:11]2=[O:27])=[CH:6][C:5]=1[F:28].O.NN>C1COCC1.C(O)C>[Br:29][C:2]([Br:1])=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][C@H:13]([CH2:15][NH:16][C:17](=[O:26])[CH3:18])[O:12][C:11]2=[O:27])=[CH:6][C:5]=1[F:28]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 88158466HCID 88158466, compound

Product 1

HCID 88158463HCID 88158463, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of Example 1D (2.45 g) in 1:1 THF/ethanol (36 mL) was heated to 70° C., treated with hydrazine monohydrate (3×227 μL) at 1 hour intervals, cooled to 25 ° C., and filtered. The filtrate was concentrated, dissolved in a mixture of pyridine (10 mL) and dichloromethane (25 mL), cooled to −5° C., treated with acetic anhydride (880 μL), warmed to room temperature, stirred for 5 minutes, and concentrated to provide the desired product. mp 177-179° C.; MS (ESI(+)) m/e 437 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 7.81 (t, 1H), 7.50 (s, 1H), 7.47 (dd, 1H), 7.20 (dd, 1H), 5.92 (br t, 1H), 4.80 (m, 1H), 4.06 (t, 1H), 3.77 (dd, 1H), 3.75-3.55 (m, 2H), 2.02 (s, 3H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. dissolutiondissolved in a mixture of pyridine (10 mL) and dichloromethane (25 mL)
  4. temperaturecooled to −5° C.
  5. additiontreated with acetic anhydride (880 μL)
  6. temperaturewarmed to room temperature
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-88c1becb5f454465b800f77da8e8c274
Source dataset
uspto-grants-2001_08
Patent number
US06277868B1

Reaction notes

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