Hydrazine hydrate (1:1) → HCID 86761311, compound

HRID 547839Notes

Reaction equation

HRID 547839 reaction equation
[C:1]([C:9]1[CH:28]=[CH:27][C:12]([CH2:13][O:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:30][NH2:31]>CO>[N:30](=[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:28]=[CH:27][C:12]([CH2:13][O:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])=[CH:11][CH:10]=1)[NH2:31]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86761309HCID 86761309, compound

Product 1

HCID 86761311HCID 86761311, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (XI) (0.7 g, 1.9 mmol) in methanol (10 ml) was treated with hydrazine hydrate (1.9 g, 38 mmol). The resulting solution was heated to a gentle reflux for 16 h., cooled and concentrated in vacuo. The residue was partitioned between DCM and water and the organic layer was collected, washed with water and dried over MgSO4. Concentration in vacuo yielded (XII) (0.7 g, 99%) as a thick cloudy white oil; δH (CDCl3, 200 MHz) 3.47 (m, 2H, N(H)CH2CH2), 3.61 (m, 2H, OCH2CH2), 4.43, 4.52 (s, 2H, ArCH2O), 5.49 (s, 2H, NNH2), 6.55 (m, 1H, CH2NHC(O)), 6.99 (m, 1H, 4″-H), 7.22 (m, 7H, 3-, 3′-, 3″-, 4′-, 5-, 5′-, 5″-H), 7.46 (m, 6H, 2-, 2′-, 2″-, 6-, 6′-, 6″-H), 7.80 (m, 1H, ArNHC(O)) ppm; υmax 3435 (N—Hstr), 1734 ((R(H)N)2C═Ostr) cm−1; m/z 389 [M+H]+ (15%), 447 [M+MeCN+NH4]+ (100%); found 389.1973, C23H25N4O2 requires 389.1978.

Workup

  1. temperatureThe resulting solution was heated to
  2. temperaturea gentle reflux for 16 h.
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between DCM and water
  6. customthe organic layer was collected
  7. washwashed with water
  8. dry with materialdried over MgSO4
  9. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-a154ed546337448887f7949e3922894c
Source dataset
uspto-grants-2011_05
Patent number
US07939581B2

Reaction notes

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