Triethylamine → HCID 86643703, compound

HRID 1672825Notes

Reaction equation

HRID 1672825 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:23]4[O:24][CH:25]=[C:26]([C:28](O)=[O:29])[N:27]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:31]=1.Cl.[CH2:33]([NH2:35])[CH3:34].C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>ClCCl.C(Cl)(Cl)Cl>[CH2:33]([NH:35][C:28]([C:26]1[N:27]=[C:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([N:14]3[CH2:13][C@H:12]4[N:8]([CH2:9][CH2:10][CH2:11]4)[C:7]4[N:31]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=4[C:15]3=[O:16])[CH:18]=2)[O:24][CH:25]=1)=[O:29])[CH3:34]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67348673HCID 67348673, compound

Product 1

HCID 86643703HCID 86643703, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-2-[3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,3-oxazole-4-carboxylic acid (105 mg, 0.240 mmol) obtained in Step 1 was dissolved in dichloromethane (5 mL), and the mixture was stirred at room temperature for 5 hours after adding ethylamine hydrochloride (39.0 mg, 0.480 mmol), triethylamine (0.067 mL, 0.480 mmol), 1-ethyl-3-(3dimethylaminopropyl)carbodiimide hydrochloride (92.0 mg, 0.480 mmol), and 1-hydroxybenzotriazole.monohydrate (37.0 mg, 0.240 mmol). The mixture was diluted with chloroform and washed with a saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give (S)—N-ethyl 2-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,3-oxazole-4-carboxamide (110 mg, quantitative).

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fa98ce991acb47df86d88799399063d3
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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