Sodium borohydride → 1,1-Dimethylethyl (6-{[6-(morpholin-4-yl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)carbamate

HRID 633491Notes

Reaction equation

HRID 633491 reaction equation
[BH4-].[Na+].Cl[C:4]1[N:8]2[N:9]=[C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1.[SH:19][C:20]1[CH:36]=[CH:35][C:23]2[N:24]=[C:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[S:26][C:22]=2[CH:21]=1>C(O)C>[N:13]1([C:10]2[CH:11]=[CH:12][C:7]3[N:8]([C:4]([S:19][C:20]4[CH:36]=[CH:35][C:23]5[N:24]=[C:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:33])[CH3:31])[S:26][C:22]=5[CH:21]=4)=[N:5][N:6]=3)[N:9]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 218221903-Chloro-6-(morpholin-4-yl)[1,2,4]triazolo[4,3-b]pyridazineHCID 468537721,1-Dimethylethyl (6-sulphanyl-1,3-benzothiazol-2-yl)carbamate

Product 1

HCID 867070071,1-Dimethylethyl (6-{[6-(morpholin-4-yl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)carbamateYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

68 mg of sodium borohydride are added to a mixture of 430 mg of 3-chloro-6-(morpholin-4-yl)[1,2,4]triazolo[4,3-b]pyridazine and 510 mg of 1,1-dimethylethyl (6-sulphanyl-1,3-benzothiazol-2-yl)carbamate in 9 cm3 of degassed ethanol and then the reaction is refluxed for 23 h. The suspension is left at 20° C. overnight and is then concentrated to dryness under vacuum. The product is chromatographed by solid deposit on a Merck cartridge of 70 g of silica 15-40 μm, elution being carried out with a gradient of 100% dichloromethane to 95/5 dichloromethane/methanol. 370 mg of 1,1-dimethylethyl (6-{[6-(morpholin-4-yl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)carbamate are thus obtained in the form of a white solid, the characteristics of which are as follows:

Workup

  1. temperaturethe reaction is refluxed for 23 h
  2. concentrationis then concentrated to dryness under vacuum
  3. customThe product is chromatographed by solid deposit on a Merck cartridge of 70 g of silica 15-40 μm, elution

Sources & evidence

ORD record
ord-5adcb00a82e14d5ba4b522aa9aa1227a
Source dataset
uspto-grants-2016_04
Patent number
US09321777B2

Reaction notes

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