Triethylamine → HCID 73053626, compound

HRID 1526503Notes

Reaction equation

HRID 1526503 reaction equation
Cl[C:2]1[C:3]2[C:10]3[CH:11]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=[CH:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl-].[N:21]1([CH:27]2[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].CCN(CC)CC>CC#N>[N:21]1([CH:27]2[CH2:28][CH2:29][CH:30]([NH:33][C:2]3[C:3]4[C:10]5[CH:11]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=[CH:14][C:9]=5[S:8][C:4]=4[N:5]=[CH:6][N:7]=3)[CH2:31][CH2:32]2)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 86707955HCID 86707955, compoundHCID 86707956HCID 86707956, compound

Product 1

HCID 73053626HCID 73053626, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 4-chlorobenzo[4,5]thieno[2,3-d]pyrimidine-6-carboxylate (500 mg, 1.7 mmol, 1.00 equiv), 4-(morpholin-4-yl)cyclohexan-1-amine chloride (1.1 g, 4.25 mmol, 2.5 equiv) and potassium carbonate (2.3 g, 17 mmol, 10.17 equiv) in CH3CN (100 mL) was Et3N (2 mL) at room temperature under nitrogen. The resulting solution was heated to reflux overnight. The solids were filtered out and the filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (10:1) to give the desired ethyl 3-[[4-(morpholin-4-yl)cyclohexyl]amino]-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5,10,12-hexaene-12-carboxylate (500 mg, 66%) as a yellow solid. LCMS: (ES, m/z) 441 [M+H]+. 1H-NMR (300 MHz, CD3OD): δ 1.44-1.53 (4H, m), 1.57-1.65 (3H, m), 2.24-2.29 (2H, m), 2.25-2.33 (3H, m), 2.56-2.67 (4H, m), 3.45-3.75 (4H, m), 4.31-4.43 (1H, m), 4.45-4.50 (2H, m), 8.07-8.16 (2H, m), 8.49 (1H, s), 8.78 (1H, s).

Workup

  1. customat room temperature
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux overnight
  4. filtrationThe solids were filtered out
  5. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-a9ec070be43a4a27a7517efe89381bbd
Source dataset
uspto-grants-2015_07
Patent number
US09085586B2

Reaction notes

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