Hydrazine hydrate (1:1) → HCID 22506178, compound

HRID 1814431Notes

Reaction equation

HRID 1814431 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][N:9]([CH:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:40][CH2:39][CH2:38]2)[CH2:10][CH2:11][CH2:12][C:13]2[N:17]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:16]=[N:15][N:14]=2)C(=O)C2=CC=CC=C12.O.NN.[Br:56][C:57]1[CH:62]=[CH:61][C:60]([N:63]=[C:64]=[O:65])=[CH:59][CH:58]=1>CCO>[Br:56][C:57]1[CH:62]=[CH:61][C:60]([NH:63][C:64](=[O:65])[NH:5][CH2:6][CH2:7][CH2:8][N:9]([CH:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:40][CH2:39][CH2:38]2)[CH2:10][CH2:11][CH2:12][C:13]2[N:17]([C:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:16]=[N:15][N:14]=2)=[CH:59][CH:58]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 756094-Bromophenyl isocyanateHCID 17964443HCID 17964443, compound

Product 1

HCID 22506178HCID 22506178, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[[(3-phthalimido)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]-1-[1-(triphenylmethyl)tetrazol-5-yl]propane (50 mg, 0.073 mmol) in EtOH (1 ml) was added hydrazine monohydrate (17 μl, 0.36 mmol), and the mixture was stirred at RT for 3 h. The reaction mixture was concentrated under vacuum, and then water was added. The mixture was extracted with chloroform, washed with brine, dried over sodium sulfate, and filtered. To the filtrate was added 4-bromophenyl isocyanate (17 mg, 0.088 mmol), and the mixture was stirred at RT for 1 h. The reaction mixture was concentrated under vacuum to dryness, and the residue was adsorbed on a plate of silica gel and then developed with 3% methanol/chloroform to afford 3-[[3-(4-bromophenylureido)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]-1-[1-(triphenylmethyl)tetrazol-5-yl]propane (Compound 217, 33 mg, 60%): MS(ES+) m/e 756 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 7.62 (m, 1H), 7.53 (br, 1H), 7.34 (m, 10H), 7.09 (m, 12H), 5.79 (br, 1H), 4.05 (m, 1H), 3.48 (m, 1H), 3.31 (m, 1H), 3.17 (m, 1H), 2.74 (m, 4H), 2.55 (m, 1H), 2.44 (m, 2H), 1.96 (m, 3H), 1.86 (m, 1H), 1.72 (m, 2H), 1.61 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionwater was added
  3. extractionThe mixture was extracted with chloroform
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. stirringthe mixture was stirred at RT for 1 h
  8. concentrationThe reaction mixture was concentrated under vacuum to dryness

Sources & evidence

ORD record
ord-b485ebfe9a36405e88dbaaa683fcf6df
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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