1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69274260, compound

HRID 2219897Notes

Reaction equation

HRID 2219897 reaction equation
[CH:1]1([NH:6][CH2:7][C:8]2[CH:17]=[C:16]3[C:11]([C@H:12]([N:18]4[CH:22]=[C:21]([CH2:23][C@@H:24]([NH:28][S:29]([C:32]5[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=5)(=[O:31])=[O:30])[C:25](O)=[O:26])[N:20]=[N:19]4)[CH2:13][CH2:14][O:15]3)=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=[N:43]C2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH4+].[Cl-].CCN=C=NCCCN(C)C>CN(C=O)C>[CH:1]1([NH:6][CH2:7][C:8]2[CH:17]=[C:16]3[C:11]([C@H:12]([N:18]4[CH:22]=[C:21]([CH2:23][C@@H:24]([NH:28][S:29]([C:32]5[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=5)(=[O:30])=[O:31])[C:25]([NH2:43])=[O:26])[N:20]=[N:19]4)[CH2:13][CH2:14][O:15]3)=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 11571042HCID 11571042, compound

Product 1

HCID 69274260HCID 69274260, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (R)-3-(1-((R)-7-((cyclopentylamino)methyl)-3,4-dihydro-2H-chromen-4-yl)-1H-1,2,3-triazol-4-yl)-2-(4-methylphenylsulfonamido)propanoic acid (61 mg, 0.11 mol), HOAt (18 mg, 0.12 mmol), i-Pr2NEt (60. mL, 0.45 mmol), NH4Cl (25 mg, 0.45 mmol), and EDCI (24 mg, 0.12 mmol) in 5 mL DMF was stirred for 24 h at RT. The reaction mixture was concentrated, taken up in H2O, and the white solid was filtered and air-dried to afford the title compound. MS (m/z, m+1): 539.4.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationthe white solid was filtered
  3. customair-dried

Sources & evidence

ORD record
ord-c4a85d39d4cd4c29b289023beb5ee4aa
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

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