Diisopropylethylamine → HCID 68510576, compound

HRID 2069461Notes

Reaction equation

HRID 2069461 reaction equation
Cl.[CH2:2]([C:4]1[CH:9]=[C:8]([C:10]2[N:14]=[C:13]([C:15]3[CH:20]=[C:19]([CH3:21])[N:18]=[C:17]([NH:22][CH:23]([CH3:25])[CH3:24])[N:16]=3)[O:12][N:11]=2)[CH:7]=[C:6]([CH3:26])[C:5]=1[CH2:27][CH2:28][C:29](O)=[O:30])[CH3:3].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:63]([NH:70][CH2:71][CH2:72][NH2:73])([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64]>CN(C=O)C.CCOC(C)=O>[C:66]([O:65][C:63](=[O:64])[NH:70][CH2:71][CH2:72][NH:73][C:29](=[O:30])[CH2:28][CH2:27][C:5]1[C:6]([CH3:26])=[CH:7][C:8]([C:10]2[N:14]=[C:13]([C:15]3[CH:20]=[C:19]([CH3:21])[N:18]=[C:17]([NH:22][CH:23]([CH3:25])[CH3:24])[N:16]=3)[O:12][N:11]=2)=[CH:9][C:4]=1[CH2:2][CH3:3])([CH3:67])([CH3:68])[CH3:69]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68508465HCID 68508465, compound

Product 1

HCID 68510576HCID 68510576, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of Intermediate 10 (25 mg, 0.061 mmol) in DMF is added DIPEA (16 μL, 0.092 mmol) followed by TBTU (23.5 mg, 0.073 mmol). The reaction mixture is stirred for 5 min before adding N-Boc-ethylenediamine (12 μL, 0.073 mmol) and stirring is continued for 2 h. The reaction mixture is diluted with EtOAc (20 mL) and is washed with sat. aq. NaHCO3 (15 mL). The org. phase is then dried over Na2SO4, filtered, and evaporated to give a yellow oil that is purified by prep. TLC (eluting with DCM/MeOH 95:5) to afford [2-(3-{2-ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-propionylamino)-ethyl]-carbamic acid tert-butyl ester (27 mg) as a white solid; LC-MS: tR=1.09 min; [M+1]+=552.30.

Workup

  1. stirringstirring
  2. waitis continued for 2 h
  3. washis washed with sat. aq. NaHCO3 (15 mL)
  4. dry with materialphase is then dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a yellow oil that
  8. customis purified by prep
  9. washTLC (eluting with DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-b78714961f6b463ca28d5970fc64bbff
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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