Diisopropylethylamine → 2-(4-{4-[5-(2-Oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-phenyl}-thiazol-2-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

HRID 737161Notes

Reaction equation

HRID 737161 reaction equation
O[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:50]([O:57][C:58]([N:60]1[CH2:64][CH2:63][CH2:62][C@H:61]1[C:65](=[O:79])[NH:66][C:67]1[S:68][CH:69]=[C:70]([C:72]2[CH:77]=[CH:76][C:75]([NH2:78])=[CH:74][CH:73]=2)[N:71]=1)=[O:59])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CN(C=O)C>[CH2:50]([O:57][C:58]([N:60]1[CH2:64][CH2:63][CH2:62][CH:61]1[C:65](=[O:79])[NH:66][C:67]1[S:68][CH:69]=[C:70]([C:72]2[CH:73]=[CH:74][C:75]([NH:78][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]3[CH:16]4[CH:11]([NH:12][C:13](=[O:14])[NH:15]4)[CH2:10][S:9]3)=[CH:76][CH:77]=2)[N:71]=1)=[O:59])[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 171548BiotinHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86616427(S)-2-[4-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 765827882-(4-{4-[5-(2-Oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-phenyl}-thiazol-2-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

70 mg (0.28 mmol) of biotin was dissolved in 5 mL of dry DMF. To this solution were added DIEA (0.34 mmol, 0.06 mL) and HATU (0.28 mmol, 0.1 g). This solution was stirred at room temperature for 2 hours. 80 mg (0.189 mmol) of Compound 5050 was then added to the reaction mixture and stirred at room temperature overnight. Reaction mixture was evaporated to dryness and redissolved in 5 mL of DMF and purified using reverse phase HPLC. MS: 649.2 (M+H+).

Workup

  1. stirringstirred at room temperature overnight
  2. customReaction mixture
  3. customwas evaporated to dryness
  4. dissolutionredissolved in 5 mL of DMF
  5. custompurified

Sources & evidence

ORD record
ord-ed3e280b401445f6909cf5d00d6e164e
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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