Diethylamine → HCID 136079972, compound

HRID 481086Notes

Reaction equation

HRID 481086 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:14]3=[N:16][N:17]([CH2:19][CH2:20]OS(C)(=O)=O)[CH:18]=[C:13]3[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1)=[O:5])[CH3:2].[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:14]3=[N:16][N:17]([CH2:19][CH2:20][N:28]([CH2:29][CH3:30])[CH2:26][CH3:27])[CH:18]=[C:13]3[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 136330642HCID 136330642, compound

Product 1

HCID 136079972HCID 136079972, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
83 °C

Procedure

To a solution of 2-(2-methanesulfonyloxy-ethyl)-4,5,6,7-tetrahydro-2H-1,2,7-triaza-cyclopenta[e]azulene-9-carboxylic acid ethyl ester (158 mg, 0.43 mmol) in CH3CN is added excess diethylamine (>3 eq) and excess K2CO3. The reaction mixture is stirred overnight at 83° C. in a sealed tube. The reaction mixture is then extracted with CH2Cl2 and washed with water. The aqueous wash is then extracted twice more with CH2Cl2. The combined extracts are dried over K2CO3 and concentrated. The crude material is purified by flash chromatography on silica gel, affording 107 mg (72%) of 2-(2-diethylamino-ethyl)-4,5,6,7-tetrahydro-2H-1,2,7-triaza-cyclopenta [e]azulene-9-carboxylic acid ethyl ester. Electrospray mass spectrum: m/z 343 [M−1]; 1H NMR (CDCl3, 300 MHz) δ8.78 (br, 1H), 7.17 (d, J=2.7 Hz, 1H), 7.15 (s, 1H), 4.27 (q, J=7.2 Hz, 2H), 4.12 (t, J=7.2 Hz, 2H), 2.91 (m, 2H), 2.81 (m, 2H), 2.65 (m, 2H), 2.59 (q, J=7.2 Hz, 4H), 1.94 (m, 2H), 1.31 (t, J=7.2 Hz, 3H), 1.02 (t, J=7.2 Hz, 6H)

Workup

  1. extractionThe reaction mixture is then extracted with CH2Cl2
  2. washwashed with water
  3. washThe aqueous wash
  4. extractionis then extracted twice more with CH2Cl2
  5. dry with materialThe combined extracts are dried over K2CO3
  6. concentrationconcentrated
  7. customThe crude material is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-0865586fcace4f849ca331b07dc16577
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

Loading…