Hydrochloric Acid → HCID 67058576, compound

HRID 470299Notes

Reaction equation

HRID 470299 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][C:19]4([CH2:25][CH2:24][N:23]([CH2:26][CH3:27])[CH2:22]4)[CH2:18]3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[N+:30]([O-])=O.Cl>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:30][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:2]=1[NH2:1])[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][C:19]3([CH2:25][CH2:24][N:23]([CH2:26][CH3:27])[CH2:22]3)[CH2:18]2)=[CH:13][CH:14]=1)=[O:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67058583HCID 67058583, compound

Product 1

HCID 67058576HCID 67058576, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

4-Amino-N-{4-[2-(7-ethyl-2,7-diaza-spiro[4.4]non-2-yl)-ethyl]-phenyl}-3-nitro-benzamide from above was dissolved in ethanol (25 ml) and 1N HCl (6 ml) to which was added 20% Pd(OH)2 and the mixture hydrogenated overnight under an atmosphere of hydrogen gas. The reaction was then filtered thru Celite and the filtrate evaporated to afford crude 3,4-Diamino-N-{4-[2-(7-ethyl-2,7-diaza-spiro[4.4]non-2-yl)-ethyl]-phenyl}-benzamide (1.18 g, 4×HCl salt) as a tan foam which was used as is in the next step.

Workup

  1. customthe mixture hydrogenated overnight
  2. filtrationThe reaction was then filtered thru Celite
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-e470f9d2e03345c98aa2df3e99b3791b
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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