Ethyl isothiocyanate → HCID 68313114, compound

HRID 1843130Notes

Reaction equation

HRID 1843130 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>>[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

5

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%

Conditions

Temperature
80 °C

Procedure

To a suspension of the compound obtained in example 1 section d (100 mg, 0.30 mmol) in CH2C2 (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. additionwere added
  2. customThen, it was evaporated to dryness
  3. customThe crude product thus obtained
  4. customwas chromatographed over silica gel
  5. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-9117d47f70e646de9a87ef29b33a9e0f
Source dataset
uspto-grants-2015_02
Patent number
US08946257B2

Reaction notes

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