N-Boc-2-isothiocyanatoethylamine → HCID 86587884, compound

HRID 1244011Notes

Reaction equation

HRID 1244011 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH2:13][NH:14][C@H:15]1[CH2:20][CH2:19][CH2:18][NH:17][C@H:16]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[N:9]([CH3:27])[C:8](=[O:28])[CH2:7][CH2:6]2.[C:29]([NH:36][CH2:37][CH2:38][N:39]=[C:40]=[S:41])([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C1C=CC=CC=1.C(OCC)C>[C:32]([O:31][C:29](=[O:30])[NH:36][CH2:37][CH2:38][NH:39][C:40]([N:17]1[CH2:18][CH2:19][CH2:20][CH:15]([NH:14][CH2:13][C:12]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][C:8](=[O:28])[N:9]3[CH3:27])=[CH:4][C:3]=2[O:2][CH3:1])[CH:16]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[S:41])([CH3:35])([CH3:33])[CH3:34]

Participants

5

Reactant 2

HCID 4219896N-Boc-2-isothiocyanatoethylamineHCID 103093706-Methoxy-1-methyl-7-[(2S,3S)-(2-phenyl-piperidin-3-ylamino)-methyl]-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 86587884HCID 86587884, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

6-Methoxy-1-methyl-7-[(2S,3S)-(2-phenyl-piperidin-3-ylamino)-methyl]-3,4-dihydro-1H-quinolin-2-one (750 mg, 1.98 mmol) and N-BOC-2-isothiocyanatoethylamine (400 mg, 1.98 mmol) were stirred in 20 mL of benzene at room temperature for 16 hours. The reaction was diluted with diethyl ether and washed 1× with water, dried over MgSO4, filtered, and concentrated. Silica gel chromatography using (6:1 ethyl acetate/hexane) gave 800 mg (70% yield) of [2-({3-[(6-Methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-ylmethyl)-amino]-2-phenyl-piperidine-1-carbothioyl}-amino)-ethyl]-carbamic acid tert-butyl ester. Rf=0.11 (6:1 ethyl acetate/hexane).

Workup

  1. washwashed 1× with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2b9bb208f20c4ccdb2ed7b1d4d9bc8be
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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