Hydrazine hydrate (1:1) → Ethyl 4-(aminomethyl)-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylate

HRID 2234011Notes

Reaction equation

HRID 2234011 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:21]([CH2:23][N:24]3C(=O)C4C(=CC=CC=4)C3=O)[N:22]=2)[CH2:14][CH2:13]1)=[O:10].O.NN>CCO>[NH2:24][CH2:23][C:21]1[N:22]=[C:18]([N:15]2[CH2:14][CH2:13][CH:12]([NH:11][C:9]([C:3]3[NH:4][C:5]([CH3:8])=[C:6]([Cl:7])[C:2]=3[Cl:1])=[O:10])[CH2:17][CH2:16]2)[S:19][C:20]=1[C:35]([O:37][CH2:38][CH3:39])=[O:36]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68579992Ethyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1,3-thiazole-5-carboxylate

Product 1

HCID 68582554Ethyl 4-(aminomethyl)-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylateYield 53.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1,3-thiazole-5-carboxylate (Example 277; 1.43 g, 2.42 mmol) in EtOH (10 ml) was added hydrazine hydrate (0.174 ml; 3.63 mmol) and refluxed for 14 h. The reaction mixture cooled to room temperature and concentrated in vacuo, diluted with DCM and acidified with 10% HCl, washed with H2O. The precipitate was filtered and dried in vacuo to give the title compound (600 mg).

Workup

  1. temperaturerefluxed for 14 h
  2. concentrationconcentrated in vacuo
  3. additiondiluted with DCM
  4. washwashed with H2O
  5. filtrationThe precipitate was filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-75d05fc756b741c7a3789cb88e02b1b3
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

Loading…