Triethylamine → Methyl 3-Cyano-2-[(2-{[(2S)-2-(3,4-dichlorophenyl)pent-4-enyl]amino}ethyl)thio]-1-naphthoate Hydrochloride

HRID 1760952노트

반응식

HRID 1760952 반응식
Cl.[NH2:2][CH2:3][CH2:4][S:5][C:6]1[C:15]([C:16]#[N:17])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[C:18]([O:20][CH3:21])=[O:19].C(N(CC)CC)C.[Cl:29][C:30]1[CH:31]=[C:32]([C@H:37]([CH2:40][CH:41]=[CH2:42])[CH:38]=O)[CH:33]=[CH:34][C:35]=1[Cl:36].C([BH3-])#N.[Na+].C([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl.C(O)(=O)C>[ClH:29].[C:16]([C:15]1[C:6]([S:5][CH2:4][CH2:3][NH:2][CH2:38][C@H:37]([C:32]2[CH:33]=[CH:34][C:35]([Cl:36])=[C:30]([Cl:29])[CH:31]=2)[CH2:40][CH:41]=[CH2:42])=[C:7]([C:18]([O:20][CH3:21])=[O:19])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)#[N:17]

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 15261880(2S)-2-(3,4-dichlorophenyl)pent-4-enalHCID 22593652Methyl 2-[(2-aminoethyl)thio]-3-cyano-1-naphthoate hydrochloride2회

생성물 1

HCID 69138873Methyl 3-Cyano-2-[(2-{[(2S)-2-(3,4-dichlorophenyl)pent-4-enyl]amino}ethyl)thio]-1-naphthoate Hydrochloride

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매2회HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl 2-[(2-aminoethyl)thio]-3-cyano-1-naphthoate hydrochloride (Intermediate 3, 530 mg, 1.65 mmol) in methanol (100 mL) was added triethylamine (250 μL, 1.82 mmol). After 30 min (2S)-2-(3,4-dichlorophenyl)pent-4-enal {Intermediate 4, 525 mg (72% pure), 1.65 mmol} and the pH was adjusted to 4-5 with acetic acid. After 30 min a solution of sodium cyanoborohydride (200 mg, 3.20 mmol) in methanol (2 mL) was added and reaction mixture stirred at ambient temperature overnight. Reaction mixture volume reduced by half and 20% K2CO3 (50 mL) was added. Reaction mixture volume reduced further to about 50 mL and methylene chloride (100 mL) was added. The organic layer was washed with brine, dried (Na2SO4), and evaporated to an oil which was chromatography on silica gel in 5% MeOH/CHCl3 to give 730 mg of the free base. The free base was dissolved in HCl/MeOH and evaporated to dryness to give 780 mg of the title compound.

후처리

  1. customreaction mixture
  2. customReaction mixture volume
  3. additionwas added
  4. customReaction mixture volume
  5. additionwas added
  6. washThe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated to an oil which

출처 및 근거

ORD 기록
ord-45c2aa06f5a541b3b82924d01f90bd04
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06846814B2

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