Diisopropylethylamine → HCID 59314331, compound

HRID 1047823Notes

Reaction equation

HRID 1047823 reaction equation
[CH3:1][S:2]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)=[O:3].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:37]([O:39][C:40]([C:42]1([NH2:51])[CH2:50][C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:43]1)=[O:41])[CH3:38].CCN(C(C)C)C(C)C>CO.C(Cl)Cl.C(Cl)Cl>[CH2:37]([O:39][C:40]([C:42]1([NH:51][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[S:2]([CH3:1])=[O:3])[CH2:50][C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:43]1)=[O:41])[CH3:38]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 3200582-(Methanesulfinyl)benzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10921653Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 59314331HCID 59314331, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a 40 mL vial containing a stirring bar, 2-(methylsulfinyl)benzoic acid (0.449 g, 2.44 mmol) is charged with dry DCM (7 mL). Stirring is initiated. HBTU (922 mg, 2.43 mmol) is added. The 2-aminoindane-2-carboxylic acid ethyl ester ([500 mg, 2.44 mmol) is added followed by DIPEA (0.95 mL, 8.0 mmol). The reaction is allowed to stir for 94 h. Analysis by tlc of the reaction mixture (silica, 10% MeOH/DCM) indicates complete consumption of the starting amine. The contents of the reaction flask are diluted with EtOAc (50 mL) and transferred to a separatory funnel. This is washed consecutively with dilute aqueous NaHCO3 (25 mL) and brine (25 mL), dried over MgSO4, filtered and evaporated in vacuo to provide 1.2 g of yellow foam. This material is dissolved in 10 mL of DCM and purified utilizing an ISCO Companion with a 40 g cartridge of silica. The gradient is 10% EtOAc in heptanes for 3 column volumes followed by a linear gradient to 100% EtOAc over 8 column volumes and then hold for 5 column volumes. 25 mL fractions are collected. Fractions 9 through 18 are combined and evaporated in vacuo to a constant weight to give 0.75 g of amorphous off-white solid.

Workup

  1. additionTo a 40 mL vial containing a stirring bar
  2. stirringto stir for 94 h
  3. customconsumption of the starting amine
  4. additionThe contents of the reaction flask are diluted with EtOAc (50 mL)
  5. customtransferred to a separatory funnel
  6. washThis is washed consecutively with dilute aqueous NaHCO3 (25 mL) and brine (25 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-ec115b69270e46d59ad27af9fb461992
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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