Triethylamine → HCID 68804537, compound

HRID 131566Notes

Reaction equation

HRID 131566 reaction equation
[OH:1][CH:2]1[CH2:6][O:5][N:4]([C:7]([C:9]2[C:17]3[C:16](=[O:18])[N:15]([CH3:19])[C:14](=[O:20])[N:13]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12]=3[S:11][C:10]=2[CH2:25]C2C3C(=CC=CC=3)N=CC=2)=[O:8])[CH2:3]1.[CH2:36]([N:38](CC)[CH2:39]C)C.O[N:44]1[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=2[N:46]=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[OH:1][CH:2]1[CH2:6][O:5][N:4]([C:7]([C:9]2[C:17]3[C:16](=[O:18])[N:15]([CH3:19])[C:14](=[O:20])[N:13]([CH2:21][CH:22]([CH3:23])[CH3:24])[C:12]=3[S:11][C:10]=2[CH2:25][N:44]2[C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=3[N:46]=[C:36]2[NH:38][CH3:39])=[O:8])[CH2:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68804289HCID 68804289, compound

Product 1

HCID 68804537HCID 68804537, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-4-Hydroxyisoxalidine hydrochloride (Example 1, part b)) (0.08 g) and triethylamine (0.09 ml) were added to a solution of the product of part b) (0.13 g) in dichloromethane (5 ml). 1-Hydroxybenzotriazole (0.09 g) was added as well as 1-ethyl-3-(3′-dimethylaminopropyl)-carbodiimide hydrochloride (0.12 g). The reaction mixture was stirred for 12 h at room temperature. The solution was concentrated under reduced pressure. The residue was purified by flash silica chromatography eluting with a gradient of 0-3% methanol in ethyl acetate. The product obtained was recrystallised from ethyl acetate/isohexane/methanol to give the title compound as a white solid (0.07 g). MS(APCI) 513.2 [M+H]+. δ 1HDMSO 0.82-0.86 (6H,m), 2-2.1 (1H, m), 2.9 (3H, m), 3.2 (3H, s), 3.6-3.68 (3H,m), 3.78-3.84 (1H, m), 3.9-3.94 (1H, m), 4-4.12 (1H, m), 4.6-4.8 (1H, 2m), 5.2-5.61 (3H, m), 6.86-6.99 (3H, m), 7.19-7.27 (2H, m)

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customThe residue was purified by flash silica chromatography
  3. washeluting with a gradient of 0-3% methanol in ethyl acetate
  4. customThe product obtained
  5. customwas recrystallised from ethyl acetate/isohexane/methanol

Sources & evidence

ORD record
ord-12122b33b855419eb17cc20049cd322d
Source dataset
uspto-grants-2008_06
Patent number
US07384950B2

Reaction notes

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