HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrazine hydrate (1:1) → 1-[5-(2-Aminoethanesulfonamido)indole-2-carbonyl]-4-[N-methyl-N-(3(1-methylethylamino)-2-pyridinyl)amino]piperidine

HRID 1449750
Notes
Print preview

Reaction equation

HRID 1449750 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][S:8]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([N:23]2[CH2:28][CH2:27][CH:26]([N:29]([CH3:40])[C:30]4[C:35]([NH:36][CH:37]([CH3:39])[CH3:38])=[CH:34][CH:33]=[CH:32][N:31]=4)[CH2:25][CH2:24]2)=[O:22])=[CH:15]3)(=[O:10])=[O:9])C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH2:6][CH2:7][S:8]([NH:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:21]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]([CH3:40])[C:30]3[C:35]([NH:36][CH:37]([CH3:38])[CH3:39])=[CH:34][CH:33]=[CH:32][N:31]=3)[CH2:25][CH2:24]1)=[O:22])=[CH:15]2)(=[O:9])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 214776561-[5-(2-Phthalimidoethanesulfonamido)indole-2-carbonyl]-4-[N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)amino]piperidine

Product 1

HCID 538450491-[5-(2-Aminoethanesulfonamido)indole-2-carbonyl]-4-[N-methyl-N-(3(1-methylethylamino)-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-[5-(2-phthalimidoethanesulfonamido)indole-2-carbonyl]-4-[N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)amino]piperidine (EXAMPLE 31, 675 mg) in 95% ethanol (10 ml) under nitrogen is added hydrazine monohydrate (53 μl). The mixture is stirred at 70°-750° for 20 hrs during which additional hydrazine monohydrate (10 μl) is added, concentrated to remove ethanol, diluted with water (10 ml), acidified to pH 2 with 1M hydrochloric acid and stirred for 10 min. The mixture is then filtered, the filtrate is adjusted to pH 10-11, and the resulting precipitate is isolated by filtration to give the title compound, NMR (CDCl3) 9.86, 7.70, 7.56, 7.29, 7.10, 6.94, 6.84, 6.68, 4.60, 4.50, 3.56, 3.44, 3.40-2.80, 2.62, 1.93, 1.65 and 1.22 δ. The b&sic filtrate is extracted with methylene chloride (2×15 ml) which is then washed with saline (10 ml), dried over sodium sulfate, and concentrated under reduced pressure to give an additional amount of the title compound.

Workup

  1. additionis added
  2. concentrationconcentrated
  3. customto remove ethanol
  4. additiondiluted with water (10 ml)
  5. filtrationThe mixture is then filtered
  6. customthe resulting precipitate is isolated by filtration

Sources & evidence

ORD record
ord-4280f4245f3443f98808dc823df62945
Source dataset
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05599930

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes