Triethylamine → HCID 178436585, compound

HRID 423960

Reaction equation

HRID 423960 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C@@H:15]([NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][C:26]=3[CH2:33][CH3:34])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:13][CH:14]=2)=[CH:6][CH:5]=1)(=[O:3])[NH2:2].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.N[C@H](C1NC=C(C2C=CC(C(N)=O)=CC=2)N=1)CC1C=CC=CC=1>C1COCC1>[NH2:32][CH2:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]([NH:23][C@H:15]([C:12]2[NH:13][CH:14]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([C:1](=[O:3])[NH2:2])=[CH:9][CH:8]=3)[N:11]=2)[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:35])=[C:26]([CH2:33][CH3:34])[CH:27]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178436584HCID 178436584, compoundHCID 178513610HCID 178513610, compound

Product 1

HCID 178436585HCID 178436585, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part E: N-{(S)-1-[4-(4-Carbamoyl-phenyl)-1H-imidazol-2-yl]-2-phenyl-ethyl}-4-cyano-2-ethyl-benzamide: 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-3baba9cdd9584b4489a3be377e7f95c1
Source dataset
uspto-grants-2012_01
Patent number
US08101778B2

Linked notes

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