Triethylamine → HCID 178436584, compound

HRID 1524874Notes

Reaction equation

HRID 1524874 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[C:4](Cl)[CH:3]=1.[CH3:13][N:14]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[CH2:40](N(CC)CC)[CH3:41].[NH2:47][C@H:48]([C:56]1[NH:57][CH:58]=[C:59]([C:61]2[CH:69]=[CH:68][C:64]([C:65]([NH2:67])=[O:66])=[CH:63][CH:62]=2)[N:60]=1)[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C1COCC1>[C:65]([C:64]1[CH:63]=[CH:62][C:61]([C:59]2[N:60]=[C:56]([C@@H:48]([NH:47][C:6](=[O:7])[C:5]3[CH:10]=[CH:11][C:2]([C:13]#[N:14])=[CH:3][C:4]=3[CH2:40][CH3:41])[CH2:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[NH:57][CH:58]=2)=[CH:69][CH:68]=1)(=[O:66])[NH2:67]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22058730Methyl 4-Bromo-2-chlorobenzoateHCID 178513610HCID 178513610, compound

Product 1

HCID 178436584HCID 178436584, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 143 Part D (90 mg, 0.51 mmol), Bop reagent (265 mg, 0.61 mmol), and triethylamine (0.42 mL, 1.5 mmol) were added together with 5 mL of THF. The mixture was stirred at RT under N2 for 15 minutes and (S)-4-(2-(1-amino-2-phenylethyl)-1H-imidazol-4-yl)benzamide prepared using the methods described in Examples 2 and 28 (365 mg, 0.51 mg) was added. The resulting mixture was heated at 75° C. for 70 minutes. The THF was removed, and the residue was dissolved in EtOAc. It was washed with waster and brine, dried over MgSO4, concentrated, and purified by flash chromatography (silica, EtOAc/hexane) to give 80 mg of the desired product. MS: 464.4 (M+1)+.

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was heated at 75° C. for 70 minutes
  3. customThe THF was removed
  4. dissolutionthe residue was dissolved in EtOAc
  5. washIt was washed with waster and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography (silica, EtOAc/hexane)

Sources & evidence

ORD record
ord-1378d686c97e4a38a6072b4f9bb76225
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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