Triethylamine → HCID 57461513, compound

HRID 1663204Notes

Reaction equation

HRID 1663204 reaction equation
[CH:1]1([CH2:7][CH:8]([N:20]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([F:31])[CH:27]=3)[N:22]=[CH:21]2)[C:9]([NH:11][C:12]2[S:13][C:14]([C:17]([OH:19])=O)=[CH:15][N:16]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:56][CH2:57][N:58](CC)[CH2:59][CH3:60]>CN(C=O)C>[CH:1]1([CH2:7][CH:8]([N:20]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([F:31])[CH:27]=3)[N:22]=[CH:21]2)[C:9]([NH:11][C:12]2[S:13][C:14]([C:17]([N:58]([CH2:59][CH3:60])[CH2:57][CH3:56])=[O:19])=[CH:15][N:16]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57461511HCID 57461511, compound

Product 1

HCID 57461513HCID 57461513, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Compound 143 (0.1 g, 0.225 mmol) and HBTU (256 mg, 0.675 mmol) was dissolved in anhydrous DMF (1 mL) and Et3N (0.125 mL, 0.9 mmol) and stirred for 30 min. To this solution was added Et2N (0.028 mL, 0.270 mmol) and the mixture was stirred at RT overnight. The reaction was poured onto ice to crash out the crude product. The product was purified via preparative HPLC. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.88-1.25 (m, 12H) 1.48-1.81 (m, 5H) 2.00-2.13 (m, 1H) 2.21-2.36 (m, 1H) 3.46 (s, 4H) 5.80 (dd, J=11.87, 4.80 Hz, 1H) 7.73-7.92 (m, 4H) 8.52 (s, 1H). [M+H] calc'd for C25H30FN5O3S, 500; found, 500.

Workup

  1. additionTo this solution was added Et2N (0.028 mL, 0.270 mmol)
  2. additionThe reaction was poured onto ice
  3. customThe product was purified via preparative HPLC

Sources & evidence

ORD record
ord-7e405689d3ff49bfa3e38ef085a33e81
Source dataset
uspto-grants-2011_10
Patent number
US08034822B2

Reaction notes

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