Triethylamine → HCID 18512165, compound

HRID 1370848Notes

Reaction equation

HRID 1370848 reaction equation
[F:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:3]=1[CH2:4][N:5]([CH2:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=2)=[CH:21][CH:20]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:7]=1[CH3:17].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[CH2:64]([O:66][C:67](=[O:71])[CH2:68][CH2:69][NH2:70])[CH3:65].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:3]=1[CH2:4][N:5]([CH2:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([NH:70][CH2:69][CH2:68][C:67]([O:66][CH2:64][CH3:65])=[O:71])=[O:29])=[CH:26][CH:25]=2)=[CH:21][CH:20]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][S:13]([CH3:16])(=[O:14])=[O:15])[C:7]=1[CH3:17]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18512269HCID 18512269, compound

Product 1

HCID 18512165HCID 18512165, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 68C (0.050 g, 0.096 mmoles), 1-hydroxybenzotriazole hydrate (0.015 g, 0.109 mmoles), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.021 g, 0.109 mmoles) in DMF (1.5 mL) were treated with β-alanine ethyl ester hydrochloride (0.121 g, 0.136 mmoles) and triethylamine (0.025 mL, 0.181 mmoles). The reaction mixture was shaken at room temperature overnight. The mixture was diluted with ethyl acetate, washed with H2O, saturated aqueous NaHCO3 (2×), 1N H3PO4 (2×), and brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by preparative HPLC (CH3CN:0.1% trifluoroacetic acid in H2O) on a YMC ODS Guardpak column to provide the title compound. 1H NMR (300 MHz, CDCl3) δ7.73 (d, 2 H), 7.25 (m, 2 H), 7.15 (m, 2 H), 6.95 (m, 6 H), 6.75 (m, 2 H), 6.15 (s, 1 H), 4.18 (q, 2 H), 4.13 (s, 2 H), 4.11 (s, 2 H), 3.73 (dd, 2 H), 2.96 (s, 3 H), 2.65 (t, 2 H), 2.30 (s, 3 H), 1.28 (t, 3 H); MS (ESI+) m/z 652 (M+H)+.

Workup

  1. washwashed with H2O, saturated aqueous NaHCO3 (2×), 1N H3PO4 (2×), and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC (CH3CN:0.1% trifluoroacetic acid in H2O) on a YMC ODS Guardpak column

Sources & evidence

ORD record
ord-3ad9d40ff0e24eeb89d64435e7de49d7
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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