Hydrazine → HCID 86760271, compound

HRID 1242084Notes

Reaction equation

HRID 1242084 reaction equation
Cl.[C:2]([O:6][C:7]([C:9]1[C:17]2[CH:16]([N:18]=[C:19]=[O:20])[CH:15]([CH2:21][N:22]3C(=O)C4C(=CC=CC=4)C3=O)[NH:14][CH2:13][C:12]=2[S:11][C:10]=1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:8])([CH3:5])([CH3:4])[CH3:3].NN>C(O)C>[C:2]([O:6][C:7]([C:9]1[C:17]2[CH:16]([N:18]=[C:19]=[O:20])[CH:15]([CH2:21][NH2:22])[NH:14][CH2:13][C:12]=2[S:11][C:10]=1[O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:8])([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86760268HCID 86760268, compound

Product 1

HCID 86760271HCID 86760271, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the above 2-benzyloxy-carbonylamino-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester hydrochloride (42 mg, 0.072 mmol) in ethanol (0.5 ml) was added hydrazine (68 μl, 0.22 mmol). The solution was stirred at 80° C. for 5 h. and at room temperature for 16 h. The mixture was filtered and the filtrate evaporated in vacuo. The residue was extracted with dichloromethane (5×1 ml). The combined dichloromethane washes were evaporated in vacuo affording 20 mg (67%) of 5-aminomethyl-2-benzyloxy-carbonylamino-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated in vacuo
  3. extractionThe residue was extracted with dichloromethane (5×1 ml)
  4. customThe combined dichloromethane washes were evaporated in vacuo

Sources & evidence

ORD record
ord-6fda25a3051e4a798a7cb73c6d5a99fe
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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