1-Hydroxybenzotriazole → (S)-2-(3,5-dimethylphenylacetamido)-3-phenyl-N-[4-(imidazo[2,1-b]benzothiazol-2-yl)phenyl]propanamide

HRID 71027Notes

Reaction equation

HRID 71027 reaction equation
C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[CH:16]1[CH:17]=[CH:18][C:19]2N(O)N=[N:22][C:20]=2[CH:21]=1.CCN(C(C)C)C(C)C.[CH3:35][C:36]1[CH:37]=[C:38]([CH2:43][C:44]([NH:46][CH:47]([CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:48](O)=[O:49])=[O:45])[CH:39]=[C:40]([CH3:42])[CH:41]=1.[N:58]1[C:59](NC2C=CC=CC=2)=[CH:60][N:61]2[C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][C:64]=3[S:63][C:62]=12>C(Cl)Cl>[CH3:42][C:40]1[CH:39]=[C:38]([CH2:43][C:44]([NH:46][C@@H:47]([CH2:51][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[C:48]([NH:22][C:20]2[CH:21]=[CH:16][C:17]([C:59]3[N:58]=[C:62]4[N:61]([CH:60]=3)[C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][C:64]=3[S:63]4)=[CH:18][CH:19]=2)=[O:49])=[O:45])[CH:37]=[C:36]([CH3:35])[CH:41]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 66592992(Imidazo[2,1-b]benzothiazol-2-yl)anilineHCID 670420812-[2-(3,5-Dimethylphenyl)acetamido]-3-phenyl-propionic acid

Product 1

HCID 51038988(S)-2-(3,5-dimethylphenylacetamido)-3-phenyl-N-[4-(imidazo[2,1-b]benzothiazol-2-yl)phenyl]propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BOP-Cl (114.5 mg, 0.450 mmol), HOBT (33.4 mg, 0.247 mmol) and DIPEA (157 μl, 0.899 mmol) were added to a solution of (S) 2-[2-(3,5-dimethylphenyl)acetamido]-3-phenyl-propanoic acid (70.0 mg, 0.225 mmol) in dry CH2Cl2 (10 ml). After 10 min 4-[(imidazo[2,1-b]benzothiazol-2-yl)aniline (65.1 mg, 0.247 mmol) was added to the solution and the reaction mixture was reflux under nitrogen for 6 h. The solvent was removed under reduced pressure and the crude mixture was purified by flash chromatography (MeOH 2.5%-CH2Cl2 97.5%) to afford the desired product (S)-2-(3,5-dimethylphenylacetamido)-3-phenyl-N-[4-(imidazo[2,1-b]benzothiazol-2-yl)phenyl]propanamide as a yellow solid (42% c.y.).

Workup

  1. temperaturethe reaction mixture was reflux under nitrogen for 6 h
  2. customThe solvent was removed under reduced pressure
  3. customthe crude mixture was purified by flash chromatography (MeOH 2.5%-CH2Cl2 97.5%)

Sources & evidence

ORD record
ord-4971729089f9428ab6a472e2066a3db5
Source dataset
uspto-grants-2014_09
Patent number
US08822698B2

Reaction notes

Loading…