HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Diisopropylethylamine → 1,1-dimethylethyl {(1R)-1-[({6-[(3-ethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-3-pyridinyl}amino)carbonyl]propyl}carbamate

HRID 527583
Notes
Print preview

Reaction equation

HRID 527583 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][C:11]([O:14][C:15]([NH:17][C@H:18]([CH2:22][CH3:23])[C:19]([OH:21])=O)=[O:16])([CH3:13])[CH3:12].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:46]([CH:48]1[C:52]2[C:53]([O:57][C:58]3[N:63]=[CH:62][C:61]([NH2:64])=[CH:60][CH:59]=3)=[CH:54][CH:55]=[CH:56][C:51]=2[CH2:50][O:49]1)[CH3:47]>CN(C)C=O>[CH2:46]([CH:48]1[C:52]2[C:53]([O:57][C:58]3[N:63]=[CH:62][C:61]([NH:64][C:19]([C@H:18]([NH:17][C:15](=[O:16])[O:14][C:11]([CH3:10])([CH3:12])[CH3:13])[CH2:22][CH3:23])=[O:21])=[CH:60][CH:59]=3)=[CH:54][CH:55]=[CH:56][C:51]=2[CH2:50][O:49]1)[CH3:47]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2755936(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acidHCID 679606476-[(3-Ethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-3-pyridinamine2×

Product 1

HCID 67966834
1,1-dimethylethyl {(1R)-1-[({6-[(3-ethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-3-pyridinyl}amino)carbonyl]propyl}carbamate
Yield 73.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

In a 8 ml vial 6-[(3-ethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-3-pyridinamine (Intermediate 108, 10 mg) was dissolved in N,N-dimethylformamide (1 ml) to give a colourless solution. DIPEA (10.22 μl, 0.059 mmol), (2R)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butanoic acid (9.52 mg, 0.047 mmol) and, finally, TBTU (15.03 mg, 0.047 mmol) were added. The reaction mixture was shaken at 60° C. After overnight shaking, the reaction was completed. The reaction mixture was evaporated under vacuum to give the crude product as a yellow oil which was purified via Biotage SP1 (with Cyclohexane/EtOAc as eluents from 2:1 to 1:1 in 10 CV; then 2:1 for 5 CV; 10 g SNAP Silica column). The collected fractions afforded the title compound as a colourless oil (12.7 mg).

Workup

  1. customto give a colourless solution
  2. stirringAfter overnight shaking
  3. customThe reaction mixture was evaporated under vacuum
  4. customto give the crude product as a yellow oil which
  5. customwas purified via Biotage SP1 (with Cyclohexane/EtOAc as eluents from 2:1 to 1:1 in 10 CV

Sources & evidence

ORD record
ord-03bb8348d8554e829b8d07bca7fcc910
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346790B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes