Triethylamine → HCID 59737520, compound

HRID 1907714Notes

Reaction equation

HRID 1907714 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH2:52][C:53]1[CH:58]=[C:57]([C:59]2[S:60][CH:61]=[CH:62][CH:63]=2)[CH:56]=[CH:55][C:54]=1[NH:64][C:65](=[O:71])[O:66][C:67]([CH3:70])([CH3:69])[CH3:68]>CN(C=O)C.CN(C)C1C=CN=CC=1>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[N:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([NH:52][C:53]3[CH:58]=[C:57]([C:59]4[S:60][CH:61]=[CH:62][CH:63]=4)[CH:56]=[CH:55][C:54]=3[NH:64][C:65](=[O:71])[O:66][C:67]([CH3:69])([CH3:68])[CH3:70])=[O:17])=[CH:9][CH:8]=2)[CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamateHCID 59737294HCID 59737294, compound

Product 1

HCID 59737520HCID 59737520, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 164 (0.275 g, 1.17 mmol) in DMF (10 mL) was added triethylamine (0.168 mL, 1.21 mmol) and BOP reagent (0.563 g, 1.27 mmol) and the mixture was stirred at room temperature for 30 min. Then amine 4 (0.309 g, 1.06 mmol) and excess triethylamine (0.443 mL, 3.18 mmol) were added and the reaction mixture was allowed to stir for 18 h at room temperature. Then 4-(dimethylamino)pyridine (catalytic amount) was added and the reaction mixture was heated to 50-60° C. for 24 h. The solution was concentrated, diluted with AcOEt, washed with saturated NaHCO3, H2O, brine, dried over MgSO4, filtered and concentrated. The resulting yellow solid was triturated from ethyl ether to give compound 165 (0.435 g, 81% yield).

Workup

  1. stirringto stir for 18 h at room temperature
  2. temperaturethe reaction mixture was heated to 50-60° C. for 24 h
  3. concentrationThe solution was concentrated
  4. additiondiluted with AcOEt
  5. washwashed with saturated NaHCO3, H2O, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting yellow solid was triturated from ethyl ether

Sources & evidence

ORD record
ord-589d03184ee24d6fa0850a8117423e16
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

Loading…