Hydrazine hydrate (1:1) → HCID 178462815, compound

HRID 1884911Notes

Reaction equation

HRID 1884911 reaction equation
[CH2:1]([N:3]1[CH:11]=[N:10][C:9]2[C:4]1=[N:5][C:6]([NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([OH:29])[CH2:25][CH2:24]1)=[N:7][C:8]=2[NH:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)[CH3:2].O.NN>CO.[Ni]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:8]2[N:7]=[C:6]([NH:22][C@H:23]3[CH2:24][CH2:25][C@H:26]([OH:29])[CH2:27][CH2:28]3)[N:5]=[C:4]3[C:9]=2[N:10]=[CH:11][N:3]3[CH2:1][CH3:2])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178462817HCID 178462817, compound

Product 1

HCID 178462815HCID 178462815, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A flask is charged with 12.15 g (30.57 mmol) of trans-4-[9-ethyl-6-(4-nitro-phenylamino)-9H-purin-2-yl-amino]-cyclohexanol in 1.15 l of methanol and kept under argon. At 40° C. Raney-Nickel is added slowly, followed by dropwise addition of 15.04 ml (50.06 mmol) of hydrazine monohydrate. After completion the reaction mixture is filtered, the filtrate concentrated and the crude product is purified by chromatography to obtain trans-4-[6-(4-amino-phenyl-amino)-9-ethyl-9H-purin-2-yl-amino]-cyclohexanol (74% yield); ESI-MS: 368 (M+H)+; tRet (HPLC) 7.48 min (method: same system as in method d, gradient 5®40% acetonitrile in 7,5 min.+12 min. 40% acetonitrile).

Workup

  1. customAt 40° C
  2. filtrationAfter completion the reaction mixture is filtered
  3. concentrationthe filtrate concentrated
  4. customthe crude product is purified by chromatography

Sources & evidence

ORD record
ord-d885b692582d436d90be9390d97f9133
Source dataset
uspto-grants-2004_07
Patent number
US06767906B2

Reaction notes

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