Acetic Acid → 1-Benzothiazol-6-yl-3-(4-cyclopropylaminomethyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80239노트

반응식

HRID 80239 반응식
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][C:20]=4[CH:21]=O)[C:11]3=[O:23])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:38]1([NH2:41])[CH2:40][CH2:39]1.C(O)(=O)C>C(Cl)(Cl)Cl.CO>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][C:20]=4[CH2:21][NH:41][CH:38]4[CH2:40][CH2:39]4)[C:11]3=[O:23])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 596362723-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-pyridine-4-carbaldehyde

생성물 1

HCID 498726531-Benzothiazol-6-yl-3-(4-cyclopropylaminomethyl-pyridin-3-yl)-imidazolidin-2-one수율 11.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

3-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-pyridine-4-carbaldehyde (I-177b: 100 mg, 0.3083 mmol) was reacted with NaBH(OAc)3 (98 mg, 0.4624 mmol), Cyclopropylamine (0.032 mL, 0.462 mmol) and acetic acid (5 mL) at room temperature for 12 hours to afford the crude product. The reaction was monitored by TLC (5% methanol in chloroform). Purification by column chromatography on silica gel (2% methanol in chloroform) followed by preparative HPLC afforded 13 mg of the product (11.6% yield).

후처리

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% methanol in chloroform)

출처 및 근거

ORD 기록
ord-5f5212f3b9934820b7b4d44641088965
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045173E1

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