Hydrazine hydrate (1:1) → 4-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine

HRID 1426172Notes

Reaction equation

HRID 1426172 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:15][C:16]2[S:17][CH:18]=[C:19]([CH2:21][CH2:22][N:23]3C(=O)C4C(=CC=CC=4)C3=O)[N:20]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CO>[NH2:23][CH2:22][CH2:21][C:19]1[N:20]=[C:16]([NH:15][C:10]2[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)[S:17][CH:18]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 166620792-(2-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)isoindoline-1,3-dione

Product 1

HCID 866397044-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(2-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)isoindoline-1,3-dione (13.8 g, 30.2 mmol) and hydrazine hydrate (3.03 g, 60.5 mmol) in methanol (150 mL) was heated at reflux for 3 hours, then cooled and concentrated. The crude residue was used in the next step without purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe crude residue was used in the next step without purification

Sources & evidence

ORD record
ord-67a7eac0111542aea895af2fc5093e86
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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