Dimethylformamide → HCID 90221230, compound

HRID 1481893Notes

Reaction equation

HRID 1481893 reaction equation
NC1C=CC(C#N)=CC=1NC[C@@](N)([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])C(O)=O.CCN=C=NCCC[N:32]([CH3:34])C.Cl.[CH:36]1[CH:37]=[CH:38][C:39]2[N:44](O)N=[N:42][C:40]=2[CH:41]=1.CC[N:48](C(C)C)[CH:49]([CH3:51])[CH3:50].CN(C=[O:59])C>C(OCC)(=O)C>[C:19]([O:18][C:16](=[O:17])[NH:48][C@@H:49]1[C:51](=[O:59])[NH:42][C:40]2[CH:41]=[CH:36][C:37]([C:34]#[N:32])=[CH:38][C:39]=2[NH:44][CH2:50]1)([CH3:20])([CH3:21])[CH3:22]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 90220259HCID 90220259, compound

Product 1

HCID 90221230HCID 90221230, compoundYield 36.26%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an ice cold solution of (S)-3-(2-amino-5-cyano-phenylamino)-2-tert-butoxycarbonyl amino-propionic acid (4.1 g, 12.812 mmol) in DMF (40 mL) was added EDCI.HCl (2.89 g, 15.125 mmol), HOBT (2.05 g, 15.125 mmol) and DIPEA (7.1 mL, 41.25 mmol). The resulting mixture was stirred for 16 h at RT and mixture was diluted with ethyl acetate and washed with water, brine and the organic solution was concentrated to give a material which was purified by silica gel chromatography to afford the title compound (1.4 g, 36.26%) as a light pink solid. LC-MS: 303.2 (M+H).

Workup

  1. washwashed with water, brine
  2. concentrationthe organic solution was concentrated
  3. customto give a material which
  4. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-1a6b5ed28d1e46a88f09910fc929f144
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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