Triethylamine → HCID 67411229, compound

HRID 909381Notes

Reaction equation

HRID 909381 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[C:12]([O:13][CH2:14][CH3:15])=[CH:11][C:10]([CH:16]2[C:25]3[C:24](=[O:26])[CH2:23][CH:22]([CH2:27][CH2:28][CH3:29])[CH2:21][C:20]=3[NH:19][C:18]([CH3:30])=[C:17]2[C:31]#[N:32])=[CH:9][C:8]=1[Br:33].C(N(CC)CC)C.[C:41](Cl)(=[O:45])[CH:42]([CH3:44])[CH3:43]>ClCCl>[Br:33][C:8]1[CH:9]=[C:10]([CH:16]2[C:25]3[C:24](=[O:26])[CH2:23][CH:22]([CH2:27][CH2:28][CH3:29])[CH2:21][C:20]=3[NH:19][C:18]([CH3:30])=[C:17]2[C:31]#[N:32])[CH:11]=[C:12]([O:13][CH2:14][CH3:15])[C:7]=1[O:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:41](=[O:45])[CH:42]([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 67413935HCID 67413935, compound

Product 1

HCID 67411229HCID 67411229, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of the product of step b (117 mg), triethylamine (81 μl) and isobutyrylchloride (24 μl) in dichloromethane (3 ml) was stirred for 17 h. The mixture was diluted with dichloromethane and washed with 0.5N aqueous HCl. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed on silicagel in heptane/EtOAc (from 1/0 to 0/1) as eluent. Yield: 69 mg. MS-ESI: [M+H]+=610.4/612.4; HPLC: Rt=19.45 min. (method 1). Diast. ratio: 5:1

Workup

  1. washwashed with 0.5N aqueous HCl
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silicagel in heptane/EtOAc (from 1/0 to 0/1) as eluent

Sources & evidence

ORD record
ord-04871a8b63c24153ab1331dd84cf579a
Source dataset
uspto-grants-2011_09
Patent number
US08017782B2

Reaction notes

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