Diisopropylethylamine → HCID 67265665, compound

HRID 1685753Notes

Reaction equation

HRID 1685753 reaction equation
C(O)=O.[CH2:4]([C:6]1[CH:11]=[C:10]([C:12]2[N:16]=[C:15]([C:17]3[S:18][C:19]([CH2:23][N:24]([CH:26]([CH3:28])[CH3:27])[CH3:25])=[C:20]([CH3:22])[CH:21]=3)[O:14][N:13]=2)[CH:9]=[C:8]([CH3:29])[C:7]=1[CH2:30][CH2:31][C:32](O)=[O:33])[CH3:5].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[CH2:67]([O:69][C:70](=[O:73])[CH2:71][NH2:72])[CH3:68]>CN(C=O)C>[CH2:67]([O:69][C:70](=[O:73])[CH2:71][NH:72][C:32](=[O:33])[CH2:31][CH2:30][C:7]1[C:8]([CH3:29])=[CH:9][C:10]([C:12]2[N:16]=[C:15]([C:17]3[S:18][C:19]([CH2:23][N:24]([CH:26]([CH3:28])[CH3:27])[CH3:25])=[C:20]([CH3:22])[CH:21]=3)[O:14][N:13]=2)=[CH:11][C:6]=1[CH2:4][CH3:5])[CH3:68]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67265313HCID 67265313, compound

Product 1

HCID 67265665HCID 67265665, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[2-ethyl-4-(5-{5-[(isopropyl-methyl-amino)-methyl]-4-methyl-thiophen-2-yl}-[1,2,4]oxadiazol-3-yl)-6-methyl-phenyl]-propionic acid formate salt (9 mg, 18 μmol) in DMF (1 mL), DIPEA (14.3 mg, 0.111 mmol) and TBTU (7 mg, 20 μmol) is added. The mixture is stirred for 5 min before glycine ethyl ester hydrochloride (3.9 mg, 28 μmol) is added. The mixture is stirred at rt for 1 h before it is separated by prep. HPLC to give the title compound (8 mg) as a pale yellow resin; LC-MS: tR=0.61 min; [M−1]−=527.19.

Workup

  1. additionis added
  2. customis separated by prep

Sources & evidence

ORD record
ord-37bf84731fd3428896ef915281724040
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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