Diisopropylethylamine → HCID 21019793, compound

HRID 1745394Notes

Reaction equation

HRID 1745394 reaction equation
NCC(NC[C:7]1S[C:9]([C:12]#N)=[CH:10][CH:11]=1)=O.C(C1C=C(C=CC=1)C[C:20]([NH:30][C:31](OC)=O)([CH2:24][CH2:25][S:26]([CH3:29])(=O)=O)[C:21]([OH:23])=[O:22])#N.[CH3:38]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CO.[CH2:73]([Cl:75])Cl>C(#N)C.CCOC(C)=O>[CH3:38][O:23][C:21](=[O:22])[CH:20]([N:30]=[CH:31][C:10]1[CH:11]=[CH:7][C:73]([Cl:75])=[CH:12][CH:9]=1)[CH2:24][CH2:25][S:26][CH3:29]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21226129Dichloromethane methanolHCID 22225780HCID 22225780, compoundHCID 22225785HCID 22225785, compound

Product 1

HCID 21019793HCID 21019793, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-amino-N-(5-cyano-thiophen-2-ylmethyl)-acetamide (150 mg, 0.485 mmol), (±)-2-(3-cyano-benzyl)-4-methanesulfonyl-2-methoxycarbonylamino-butyric acid (172 mg, 0.485 mmol), HATU (369 mg, 0.97 mmol), and DIEA (178 μL, 0.97 mmol) in acetonitrile (5.0 mL) was stirred at rt overnight. The solution was diluted with EtOAc (20 mL) washed with HCl (1M, 10 mL), NaHCO3 (sat., 10 mL), brine (10 mL), and removed in vacuo to give an oil. Column chromatography (MeOH/CH2Cl2, 5:95) gave an oil corresponding to the title compound (100 mg, 39%), MS (electrospray) 532 (M+1). (±)-[1-(3-Carbamimidoyl-benzyl)-1-({[(5-carbamimidoyl-thiophen-2-ylmethyl)-carbamoyl]-methyl}-carbamoyl)-3-methanesulfonyl-propyl]-carbamic acid methyl ester. (Compound 4)

Workup

  1. washwashed with HCl (1M, 10 mL), NaHCO3 (sat., 10 mL), brine (10 mL)
  2. customremoved in vacuo
  3. customto give an oil

Sources & evidence

ORD record
ord-12c1c21a9b2f4c369234aac62ad5f5b5
Source dataset
uspto-grants-2006_03
Patent number
US07019019B2

Reaction notes

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