Sodium borohydride → 1-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}-3-(6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)urea

HRID 633483

Reaction equation

HRID 633483 reaction equation
Cl[C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[CH3:18][C@H:19]1[O:24][C@@H:23]([CH3:25])[CH2:22][N:21]([CH2:26][CH2:27][NH:28][C:29]([NH:31][C:32]2[S:33][C:34]3[CH:40]=[C:39]([SH:41])[CH:38]=[CH:37][C:35]=3[N:36]=2)=[O:30])[CH2:20]1.[BH4-].[Na+]>C(N(CC)CC)C>[CH3:25][C@H:23]1[O:24][C@@H:19]([CH3:18])[CH2:20][N:21]([CH2:26][CH2:27][NH:28][C:29]([NH:31][C:32]2[S:33][C:34]3[CH:40]=[C:39]([S:41][C:2]4[N:6]5[N:7]=[C:8]([C:11]6[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=6)[CH:9]=[CH:10][C:5]5=[N:4][N:3]=4)[CH:38]=[CH:37][C:35]=3[N:36]=2)=[O:30])[CH2:22]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 446043783-Chloro-6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazineHCID 866478781-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea

Product 1

HCID 251830191-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}-3-(6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)ureaYield 16.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The 1-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}-3-(6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)urea was prepared according to the method described in Example 1a, but using 186 mg of 3-chloro-6-(4-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine, 366 mg of 1-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea, 0.14 cm3 of triethylamine and 38 mg of sodium borohydride. 73 mg of 1-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}-3-(6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)urea are thus obtained in the form of a beige powder, the characteristics of which are as follows:

Workup

  1. customThe 1-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}-3-(6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)urea was prepared

Sources & evidence

ORD record
ord-61faf524883e4d1196fead101dc74993
Source dataset
uspto-grants-2016_04
Patent number
US09321777B2

Linked notes

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