Ethyl isothiocyanate → HCID 68313114, compound

HRID 1887025Notes

Reaction equation

HRID 1887025 reaction equation
O=[C:2]1[NH:10][C:9]2[C:4](=[N:5][C:6]([C:11]3[CH:12]=[N:13][N:14]4[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=34)=[N:7][CH:8]=2)[N:3]1[CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[CH2:28]([N:30]=C=S)[CH3:29].CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:28]([NH:30][C:2]1[N:3]([CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[C:4]2[C:9]([N:10]=1)=[CH:8][N:7]=[C:6]([C:11]1[CH:12]=[N:13][N:14]3[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=13)[N:5]=2)[CH3:29]

Participants

6

Reactant 4

HCID 10966Ethyl isothiocyanateHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 52933409HCID 52933409, compound

Product 1

HCID 68313114HCID 68313114, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of the compound obtained in example 1 section d (100 mg, 0.30 mmol) in CH2Cl2 (2 mL), ethyl isothiocyanate (0.042 ml, 0.48 mmol), EDC.HCl (171 mg, 0.89 mmol) and DIPEA (0.25 ml, 1.49 mmol) were added. The reaction mixture was heated in a CEM Explorer microwave oven at 80° C. and 150 W for 30 min. Then, it was evaporated to dryness. The crude product thus obtained was chromatographed over silica gel using MeOH/EtOAc mixtures of increasing polarity as eluent, to afford 42 mg of the desired compound (36% yield).

Workup

  1. customThen, it was evaporated to dryness
  2. customThe crude product thus obtained
  3. customwas chromatographed over silica gel
  4. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-1a4b15ca68cb4ac29911510696ed07a5
Source dataset
uspto-grants-2013_08
Patent number
US08501735B2

Reaction notes

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