Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (S)-2-(3,5-dimethylphenylacetamido)-3-phenyl-N-[4-(7-(2-morpholin-4-yl-ethoxy)-imidazo[2,1-b]benzothiazol-2-yl)phenyl]propanamide

HRID 71029Notes

Reaction equation

HRID 71029 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@@H:13]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14](O)=[O:15])=[O:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[N:24]1([CH2:30][CH2:31][O:32][C:33]2[CH:51]=[CH:50][C:36]3[N:37]4[CH:42]=[C:41]([C:43]5[CH:49]=[CH:48][C:46]([NH2:47])=[CH:45][CH:44]=5)[N:40]=[C:38]4[S:39][C:35]=3[CH:34]=2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@@H:13]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:14]([NH:47][C:46]2[CH:45]=[CH:44][C:43]([C:41]3[N:40]=[C:38]4[N:37]([CH:42]=3)[C:36]3[CH:50]=[CH:51][C:33]([O:32][CH2:31][CH2:30][N:24]5[CH2:25][CH2:26][O:27][CH2:28][CH2:29]5)=[CH:34][C:35]=3[S:39]4)=[CH:49][CH:48]=2)=[O:15])=[O:11])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 445986692-(4-Aminophenyl)-7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b]-[1,3]benzothiazoleHCID 67042063HCID 67042063, compound

Product 1

HCID 51038974(S)-2-(3,5-dimethylphenylacetamido)-3-phenyl-N-[4-(7-(2-morpholin-4-yl-ethoxy)-imidazo[2,1-b]benzothiazol-2-yl)phenyl]propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
155 °C

Procedure

Working as in the example 4, but using (S)-2-(2-(3,5-dimethylphenyl)acetamido)-3-phenyl-propionic acid and [4-(7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b]benzothiazol-2-yl]aniline and reagents as HATU and DIPHEA in dry DMF. The reaction mixture was stirred at room temperature for 6 h, at 70° C. for 48 h and at 155° C. for 24 h. Then the solvent was removed under reduced pressure and the crude mixture was purified by flash chromatography to give the desired product (S)-2-(3,5-dimethylphenylacetamido)-3-phenyl-N-[4-(7-(2-morpholin-4-yl-ethoxy)-imidazo[2,1-b]benzothiazol-2-yl)phenyl]propanamide

Workup

  1. customThen the solvent was removed under reduced pressure
  2. customthe crude mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-f157c2c822394b9d8657eb2f9a53d913
Source dataset
uspto-grants-2014_09
Patent number
US08822698B2

Reaction notes

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