Sodium borohydride → 1-{6-[(6-Ethoxy-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea

HRID 633505Notes

Reaction equation

HRID 633505 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([S:15][C:16]3[CH:36]=[CH:35][C:19]4[N:20]=[C:21]([NH:23][C:24]([NH:26][CH2:27][CH2:28][N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)=[O:25])[S:22][C:18]=4[CH:17]=3)=[N:13][N:14]=2)[N:11]=1)[CH3:4]>C(O)C>[CH2:3]([O:5][C:6]1[CH2:7][CH2:8][C:9]2[N:10]([C:12]([S:15][C:16]3[CH:36]=[CH:35][C:19]4[N:20]=[C:21]([NH:23][C:24]([NH:26][CH2:27][CH2:28][N:29]5[CH2:30][CH2:31][O:32][CH2:33][CH2:34]5)=[O:25])[S:22][C:18]=4[CH:17]=3)=[N:13][N:14]=2)[N:11]=1)[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 425986581-{6-[(6-Ethoxy[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea

Product 1

HCID 425986591-{6-[(6-Ethoxy-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]ureaYield 40.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

27 mg of sodium borohydride are added to a mixture of 179 mg of 1-{6-[(6-ethoxy[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea in 10 cm3 of ethanol. The reaction is refluxed for 3.5 h, and then 108 mg of sodium borohydride are added gradually and the reflux is maintained for 48 h. The reaction mixture is concentrated to dryness under reduced pressure. The residue is purified by chromatography on Biotage Quad 12/25 (KP-SIL, 60 A; 32-63 mM), elution being carried out with a dichloromethane/methanol gradient of 99/1 to 93/7. 72 mg of 1-{6-[(6-ethoxy-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea are thus obtained in the form of a white powder, the characteristics of which are as follows:

Workup

  1. temperatureThe reaction is refluxed for 3.5 h
  2. temperaturethe reflux is maintained for 48 h
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  4. customThe residue is purified by chromatography on Biotage Quad 12/25 (KP-SIL, 60 A
  5. wash32-63 mM), elution

Sources & evidence

ORD record
ord-33af7b5a24fc41c4aedc017f42e13d85
Source dataset
uspto-grants-2016_04
Patent number
US09321777B2

Reaction notes

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