Triethylamine → N1-[3-(2-{[(Ethylamino)carbonyl]amino}-1,3-benzothiazol-6-yl)-3-oxopropyl]-2,5-difluorobenzamide

HRID 9143

Reaction equation

HRID 9143 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([C:6]1[CH:20]=[CH:19][C:9]2[N:10]=[C:11]([NH:13][C:14]([NH:16][CH2:17][CH3:18])=[O:15])[S:12][C:8]=2[CH:7]=1)=[O:5].C(N(CC)CC)C.[F:28][C:29]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:30]=1[C:31](Cl)=[O:32]>CN(C=O)C>[CH2:17]([NH:16][C:14]([NH:13][C:11]1[S:12][C:8]2[CH:7]=[C:6]([C:4](=[O:5])[CH2:3][CH2:2][NH:1][C:31](=[O:32])[C:30]3[CH:34]=[C:35]([F:38])[CH:36]=[CH:37][C:29]=3[F:28])[CH:20]=[CH:19][C:9]=2[N:10]=1)=[O:15])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5880822,5-Difluorobenzoyl chlorideHCID 219855561-(6-(3-Aminopropanoyl)-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 21985558N1-[3-(2-{[(Ethylamino)carbonyl]amino}-1,3-benzothiazol-6-yl)-3-oxopropyl]-2,5-difluorobenzamideYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Similar to the synthesis of Example 249, a mixture of 1-(6-(3-aminopropanoyl)-2-benzothiazolyl)-3-ethylurea, triethylamine and 2,5-difluorobenzoyl chloride in DMF was reacted to give the desired compound 0.019 g (22%). LC/MS 433.0 (M+1); LC retention time 2.94 min.

Workup

  1. customSimilar to the synthesis of Example 249
  2. customwas reacted

Sources & evidence

ORD record
ord-f1d1a30eab97407f8e26262ae5a1d46f
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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