Cesium carbonate → HCID 178484192, compound

HRID 1893377Notes

Reaction equation

HRID 1893377 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][NH:12][CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[CH:24]=[C:23]([CH3:25])[O:22][N:21]=2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[CH3:35][NH:36][CH2:37][CH2:38]Cl>C(#N)C>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH2:38][CH2:37][NH:36][CH3:35])[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:15][CH2:16][C@H:17]([C:20]2[CH:24]=[C:23]([CH3:25])[O:22][N:21]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 3028223Ethanamine, 2-chloro-N-methyl-, hydrochloride (1:1)HCID 178426061HCID 178426061, compound

Product 1

HCID 178484192HCID 178484192, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of trans-8-chloro-1-[4-(5-methyl-isoxazol-3-yl)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (50.0 mg, 0.130 mmol), cesium carbonate (170 mg, 0.521 mmol) and 2-methylaminoethyl chloride hydrochloride (67.7 mg, 0.521 mmol) in acetonitrile (1.3 ml) was heated at 70° C. for 20 h. After cooling to room temperature the reaction mixture was partitioned between 1 M aqueous sodium hydroxide solution (2 ml) and ethyl acetate (5 ml). The layers were separated. The aqueous layer was extracted with three 5-ml portions of ethyl acetate. The combined organic layers were concentrated in vacuo. Preparative RP-HPLC with water (0.05% formic acid)/methanol as eluent gave the hydroformate salt of the title compound, which was liberated by filtration over aminopropyl modified silica gel (10 g) with methanol (20 ml) as eluent. The filtrate was concentrated to dryness. The residue was redissolved in ethyl acetate, filtrated over cotton wool and concentrated to dryness to give the title compound (38 mg, 66%) as off-white solid. MS m/e: 441 ([M+H]+).

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas partitioned between 1 M aqueous sodium hydroxide solution (2 ml) and ethyl acetate (5 ml)
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted with three 5-ml portions of ethyl acetate
  5. concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-33ae86c949674fd6b06a3984dff60045
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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