Bromine → N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyanocyclopropyl)benzamide

HRID 2190399Notes

Reaction equation

HRID 2190399 reaction equation
[S-:1][C:2]#[N:3].[K+].[NH2:5][C:6]1[CH:32]=[CH:31][C:9]([O:10][C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:30])[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4([C:28]#[N:29])[CH2:27][CH2:26]4)[CH:20]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1.BrBr>C(O)(=O)C>[NH2:3][C:2]1[S:1][C:7]2[CH:8]=[C:9]([O:10][C:11]3[CH:12]=[C:13]([NH:17][C:18](=[O:30])[C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]5([C:28]#[N:29])[CH2:26][CH2:27]5)[CH:20]=4)[CH:14]=[CH:15][CH:16]=3)[CH:31]=[CH:32][C:6]=2[N:5]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 67312701N-[3-(4-aminophenoxy)phenyl]-3-(1-cyanocyclopropyl)benzamide

Product 1

HCID 86655364N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyanocyclopropyl)benzamideYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Using potassium thiocyanate (5.52 g, 56.8 mmol), acetic acid (380 mL), N-[3-(4-aminophenoxy)phenyl]-3-(1-cyanocyclopropyl)benzamide (5.25 g), and bromine (3.15 g, 19.7 mmol) as starting materials, and in the same manner as in Example A12(iv), the title compound (4.2 g, total of 2 steps 78%) was obtained as a yellow amorphous substance. The obtained compound was used in the next reaction without a further purification.

Sources & evidence

ORD record
ord-55552b29ad784d678b8e74ac509a63ed
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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