Diisopropylethylamine → HCID 10461269, compound

HRID 968811Notes

Reaction equation

HRID 968811 reaction equation
[C:1]([C:3]1[CH:36]=[CH:35][C:6]([CH2:7][C@@:8]2([CH3:34])[N:12]3[C:13]([S:16]([NH:19][C@@H:20]([CH3:24])[C:21]([OH:23])=O)(=[O:18])=[O:17])=[CH:14][N:15]=[C:11]3[N:10]([C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=3)[C:9]2=[O:33])=[CH:5][CH:4]=1)#[N:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.Cl.[NH2:71][CH2:72][C:73]([NH2:75])=[O:74].C(N(CC)C(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[C:73]([CH2:72][NH:71][C:21](=[O:23])[C@@H:20]([NH:19][S:16]([C:13]1[N:12]2[C@@:8]([CH2:7][C:6]3[CH:35]=[CH:36][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)([CH3:34])[C:9](=[O:33])[N:10]([C:25]3[CH:26]=[C:27]([Cl:32])[CH:28]=[C:29]([Cl:31])[CH:30]=3)[C:11]2=[N:15][CH:14]=1)(=[O:17])=[O:18])[CH3:24])(=[O:74])[NH2:75]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2723639Glycinamide hydrochlorideHCID 2724699PyBOPHCID 59979225HCID 59979225, compound

Product 1

HCID 10461269HCID 10461269, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The above carboxylic acid (0.05 g, 0.091 mmol) was dissolved in anhydrous DMF (2 mL) and benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate (PyBOP) (0.071 g, 0.137 mmol) was added to the reaction solution. The reaction mixture was stirred at room temperature for 10 min and glycinamide hydrochloride (0.015 g, 0.137 mmol) was added to the mixture followed by N,N-diisopropylethylamine (0.039 mL, 0.227 mmol). The reaction mixture was stirred at room temperature for another 15 min. The mixture was then diluted with EtOAc (10 mL) and washed with water (×2), 1N HCl, saturated NaHCO3 and then water (×1). The organic phase was dried over Na2SO4 and concentrated. The crude product was purified by silica gel preparative thin layer chromatography using CH2Cl2-MeOH (95:5) as an eluent to afford 0.043 g of the title compound as a white foam (M+1, 604.2).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for another 15 min
  2. washwashed with water (×2), 1N HCl, saturated NaHCO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel preparative thin layer chromatography

Sources & evidence

ORD record
ord-81913702e618413ab55a68969aac8145
Source dataset
uspto-grants-2007_12
Patent number
US07304067B2

Reaction notes

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