2-Ethylhexylamine → HCID 21093905, compound

HRID 1767574Notes

Reaction equation

HRID 1767574 reaction equation
[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][NH2:5])[CH3:2].C(N(C(C)C)CC)(C)C.[Cl:19][C:20]1[CH:28]=[CH:27][C:26]([N:29]2[C:34](=[O:35])[NH:33][C:32](=[O:36])[CH:31]=[N:30]2)=[CH:25][C:21]=1[C:22](Cl)=[O:23].CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O>ClC(Cl)C.C1COCC1>[Cl:19][C:20]1[CH:28]=[CH:27][C:26]([N:29]2[C:34](=[O:35])[NH:33][C:32](=[O:36])[CH:31]=[N:30]2)=[CH:25][C:21]=1[C:22]([NH:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:6][CH2:7][CH2:8][CH3:9])=[O:23]

Participants

7

Reactant 4

HCID 77192-EthylhexylamineHCID 81531DiisopropylethylamineHCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)HCID 21093904HCID 21093904, compound

Product 1

HCID 21093905HCID 21093905, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-ethylhexylamine (15 mg, 0.125 mmol) in dichloroethane (1 ml) was added diisopropylethylamine resin (60 mg, 0.225 mmol) followed by a solution of 2-chloro-5-(3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-benzoyl chloride (21 mg, 0.075 mmol) in a 3:1 mixture of dichloroethane and THF (15 ml). The reaction mixture was shaken for 16 hours and filtered. The filtrate was treated with MP-carbonate resin (75 mg, 0.225 mmol) and the resulting mixture was shaken for 3 hours. The mixture was filtered and the resin washed with dichloromethane followed by 9:1 methanol/acetic acid. The combined filtrates were concentrated under reduced pressure to give the title compound as an amorphous solid. Mass spec [M−1] 3:1 ratio of 377.2 and 379.2; 1H nmr (500 MHz, CDCl3) δ 0.92 (t, 3H), 0.96 (t, 3H), 1.26–1.66 (m, 9H), 3.46 (m, 2H), 6.26 (broad s, 1H), 7.51 (d, 1H), 7.59–7.62 (m, 2H), 7.94 (s, 1H), 8.72 (broad s, 1H).

Workup

  1. filtrationfiltered
  2. stirringthe resulting mixture was shaken for 3 hours
  3. filtrationThe mixture was filtered
  4. washthe resin washed with dichloromethane
  5. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-cb6fdbbd4ccd42099d78f2d66d5ac89f
Source dataset
uspto-grants-2007_06
Patent number
US07235549B2

Reaction notes

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