Triethylamine → HCID 57513830, compound

HRID 2368416Notes

Reaction equation

HRID 2368416 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([NH:8][C:9]([CH3:28])([CH3:27])[C:10]([NH:12][C:13]2[S:14][C:15]([C:24](O)=[O:25])=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:17]=2)=[O:11])=[O:7])=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[C:62]([N:69]1[CH2:74][CH2:73][NH:72][CH2:71][CH2:70]1)([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63]>CN(C=O)C>[C:65]([O:64][C:62]([N:69]1[CH2:74][CH2:73][N:72]([C:24]([C:15]2[S:14][C:13]([NH:12][C:10](=[O:11])[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:29]=[CH:30][C:2]([F:1])=[CH:3][CH:4]=3)([CH3:27])[CH3:28])=[N:17][C:16]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:25])[CH2:71][CH2:70]1)=[O:63])([CH3:68])([CH3:66])[CH3:67]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57513829HCID 57513829, compound

Product 1

HCID 57513830HCID 57513830, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[2-(4-Fluoro-benzoylamino)-2-methyl-propionylamino]-4-phenyl-thiazole-5-carboxylic acid (46 mg, 0.11 mmol), HBTU (50 mg, 0.13 mmol), triethylamine (22 uL, 0.16 mmol) and N-Boc piperazine (27 mg, 0.15 mmol) in DMF (2 mL) was stirred at RT for 18 h and partitioned between ethyl acetate and aq. K2CO3. The organic extract was dried over MgSO4, concentrated and chromatographed to give the title compound. m/z 596.2 (MH+).

Workup

  1. custompartitioned between ethyl acetate and aq. K2CO3
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed

Sources & evidence

ORD record
ord-262c56648adf4f25a7092e15327ffacb
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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