Diisopropylethylamine → Tert-butyl (2-(7-oxo-7-((pyridin-3-ylmethyl)amino)heptanamido)phenyl)carbamate

HRID 2276697Notes

Reaction equation

HRID 2276697 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=[N:41][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[CH2:51][N:52](C(C)C)C(C)C>CN(C=O)C>[O:24]=[C:22]([NH:52][CH2:51][C:39]1[CH:40]=[N:41][CH:36]=[CH:37][CH:38]=1)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:16]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 95435387-((2-((Tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoic acid

Product 1

HCID 90398241Tert-butyl (2-(7-oxo-7-((pyridin-3-ylmethyl)amino)heptanamido)phenyl)carbamateYield 79.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-((2-((tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoic acid (1.2 g, 3.42 mmol) in DMF (10 mL) were added HBTU (1.43 g, 3.76 mmol), DIEA (1.3 g, 10.3 mmol) at room temperature. The resulting mixture was stirred for 10 min, then tpyridin-3-ylmethanamine (1.43 g, 3.76 mmol) was added to the reaction solution. The reaction mixture was stirred for 12 h at room temperature. The reaction was quenched with water (100 mL). The resulting mixture was extracted by EtOAc (100 mL×2). The organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure. The resulting solid was purified by column chromatography (elute: EtOAc:MeOH=100:1) to afford desired compound (1.2 g, yield 79.7%) as an off-white solid.

Workup

  1. additiontpyridin-3-ylmethanamine (1.43 g, 3.76 mmol) was added to the reaction solution
  2. stirringThe reaction mixture was stirred for 12 h at room temperature
  3. customThe reaction was quenched with water (100 mL)
  4. extractionThe resulting mixture was extracted by EtOAc (100 mL×2)
  5. dry with materialdried with anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting solid was purified by column chromatography (elute: EtOAc:MeOH=100:1)

Sources & evidence

ORD record
ord-c1200769f06e4f3d99fe905f76b44db4
Source dataset
uspto-grants-2015_09
Patent number
US09133105B2

Reaction notes

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