Triethylamine → HCID 49787454, compound

HRID 244360Notes

Reaction equation

HRID 244360 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:23]=[C:24]([CH3:26])[CH:25]=1)[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[S:14]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)(=[O:16])=[O:15].[C:27](Cl)(=[O:30])[CH2:28][CH3:29].C(N(CC)CC)C>>[CH3:26][C:24]1[CH:23]=[C:4]([CH:3]=[C:2]([CH3:1])[CH:25]=1)[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[S:14]([N:17]1[CH2:22][CH2:21][N:20]([C:27](=[O:30])[CH2:28][CH3:29])[CH2:19][CH2:18]1)(=[O:16])=[O:15]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 10133817HCID 10133817, compound

Product 1

HCID 49787454HCID 49787454, compound

Procedure

To a solution of compound 24 (0.102 g, 0.27 mmol) in CH2Cl, (2 mL) was added propionyl chloride (0.035 g, 0.38 mmol) and triethylamine (0.039 g, 0.38 mmol). The reaction mixture was stirred at room temperature for 20 hrs, whereupon the starting material was consumed (TLC, 1% MeOH in CH2Cl2). The reaction mixture was concentrated in vacuo, redissolved in a minimal amount of CH2Cl2, and chromatographed over normal phase silica (MeOH/CH2Cl2). The fractions containing the desired product were combined and concentrated in vacuo to yield a white powder, which was then triturated with CH2Cl2/diisopropyl ether and vacuum filtered to yield the desired product as a powder. The powder was redissolved in CH2Cl2 and chromatographed for a second time over normal phase silica (MeOH/CH2Cl2). The fractions containing the desired product were combined and concentrated in vacuo to yield a white powder. The powder was triturated with diisopropyl ether and vacuum filtered to yield compound 57 (0.061 g, 52.1% yield, 96.6% HPLC purity). 1H NMR (500 MHz, CDCl3): 8.27 (d, J=2 Hz, 1H), 7.67 (dd, J1=9 Hz, J2=2 Hz, 1H), 6.94 (s, 1H), 6.90 (d, J=9 Hz, 1H), 6.68 (s, 2H), 3.71 (m, 2H), 3.54 (m, 2H), 3.35 (m, 4H), 2.34 (s, 6H), 2.32 (m, 2H), 1.13 (t, J=7 Hz, 3H); MS (ESI, EI+): m/z=428 (MH+).

Workup

  1. customwas consumed (TLC, 1% MeOH in CH2Cl2)
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionredissolved in a minimal amount of CH2Cl2
  4. customchromatographed over normal phase silica (MeOH/CH2Cl2)
  5. additionThe fractions containing the desired product
  6. concentrationconcentrated in vacuo
  7. customto yield a white powder, which
  8. customwas then triturated with CH2Cl2/diisopropyl ether and vacuum
  9. filtrationfiltered

Sources & evidence

ORD record
ord-99a8a7cfa1164e928523a80b31f33d86
Source dataset
uspto-grants-2014_02
Patent number
US08658642B2

Reaction notes

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