Chloroform → 4-azido-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-2-amine

HRID 1803271Notes

Reaction equation

HRID 1803271 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].FC(F)(F)C(O)=O.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:26][C:27]2[S:28][C:29]3[CH2:35][CH2:34][CH2:33][C:32]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)(O)[C:30]=3[N:31]=2)[CH:17]=[CH:18][C:19]=1[N:20]1[CH:24]=[N:23][C:22]([CH3:25])=N1.C(Cl)(Cl)[Cl:44]>>[N:1]([C:32]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:30]2[N:31]=[C:27]([NH:26][C:16]3[CH:17]=[CH:18][C:19]([N:20]4[CH:25]=[C:22]([Cl:44])[N:23]=[CH:24]4)=[C:14]([O:13][CH3:12])[CH:15]=3)[S:28][C:29]=2[CH2:35][CH2:34][CH2:33]1)=[N+:2]=[N-:3]

Participants

5

Reactant 4

HCID 6212Chloroform2×HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 581100282-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-4-ol

Product 1

HCID 866499284-azido-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-2-amineYield 57%

Procedure

Sodium azide (4.5 mg, 0.069 mml) and trifluoroacetic acid were sequentially added to a solution of 2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-4-ol (10 mg, 0.023 mmol, from example 81) in chloroform (0.1 mL). After stirring 4 h at rt, the reaction was diluted with chloroform and washed with saturated sodium bicarbonate solution. The organic layer was concentrated in vacuo to afford 4-azido-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-2-amine (6 mg, 57% yield). LC-MS (M+H)+ 459.33.

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-3a102d08131d46dea346a7c1afd92938
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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