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 1035776Notes

Reaction equation

HRID 1035776 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-c7e8d2680e7b4a9dbea8e47beea78cd7
Source dataset
uspto-grants-2013_10
Patent number
US08546393B2

Reaction notes

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