Triethylamine → HCID 70032059, compound

HRID 1264634Notes

Reaction equation

HRID 1264634 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:12]=2[CH:13]=1.Cl.CS[C:22](SC)=[C:23]([C:26](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[Cl:33])[C:24]#[N:25].[NH2:37][C@H:38]1[CH2:44][CH2:43][CH2:42][CH2:41][N:40]([CH2:45][C:46]([N:48]2[CH2:52][CH2:51][CH2:50][CH2:49]2)=[O:47])[C:39]1=[O:53]>C(#N)C>[Cl:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:26](=[O:34])[C:23]([C:24]#[N:25])=[C:22]([NH:37][C@H:38]1[CH2:44][CH2:43][CH2:42][CH2:41][N:40]([CH2:45][C:46]([N:48]2[CH2:49][CH2:50][CH2:51][CH2:52]2)=[O:47])[C:39]1=[O:53])[NH:18][C:15]1[CH:16]=[CH:17][C:11]2[O:10][C:9]([CH3:8])=[CH:13][C:12]=2[CH:14]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 28190912-(2-Chlorobenzoyl)-3,3-bis(methylsulfanyl)prop-2-enenitrileHCID 12047820(S)-1-[(3-amino-hexahydro-2-oxo-1H-azepin-1-yl)acetyl]pyrrolidineHCID 216968662-Methyl-1-benzofuran-5-amine--hydrogen chloride (1/1)

Product 1

HCID 70032059HCID 70032059, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Triethylamine (0.04 mL, 0.29 mmol) was added to a suspension of 2-methyl-5-benzofuranamine·HCl (40 mg, 0.22 mmol) and acetonitrile (0.5 mL) at room temperature, which resulted in a clear solution. To the solution was added α-[bis(methylthio)methylene]-2-chloro-β-oxobenzenepropanenitrile(56 mg, 0.20 mmol) and the resulting solution was heated at 50° C. for 1 hour. To this mixture was added 1-[[(3S)-3-aminohexahydro-2-oxo-1H-azepin-1-yl]acetyl]pyrrolidine (47 mg, 0.20 mmol) and the resulting mixture was heated at 70° C. After 4 h, the mixture was concentrated in vacuo. The residue was purified by flash chromatography (silica, 0 to 2% methanol/dichloromethane) to give the title compound as a white solid (44 mg, 39%): MS (ESI, pos. ion spectrum) m/z 574/576 (M+H); HPLC (method A) tR 4.03 min.

Workup

  1. customwhich resulted in a clear solution
  2. temperaturethe resulting mixture was heated at 70° C
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe residue was purified by flash chromatography (silica, 0 to 2% methanol/dichloromethane)

Sources & evidence

ORD record
ord-fbb2e25324634e06bebe94cd3ba3d055
Source dataset
uspto-grants-2003_04
Patent number
US06544981B2

Reaction notes

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