Formamidine acetate → Benzyl 3-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)azetidine-1-carboxylate

HRID 1972946노트

반응식

HRID 1972946 반응식
[NH2:1][N:2]1[C:6]([C:7]#[N:8])=[CH:5][CH:4]=[C:3]1[CH:9]1[CH2:12][N:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:10]1.C(O)(=O)C.[CH:27](N)=[NH:28]>C(O)CCC>[NH2:8][C:7]1[C:6]2=[CH:5][CH:4]=[C:3]([CH:9]3[CH2:10][N:11]([C:13]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:14])[CH2:12]3)[N:2]2[N:1]=[CH:27][N:28]=1

참가 물질

4

반응물 2

HCID 160693Formamidine acetateHCID 58529445benzyl 3-(1-amino-5-cyano-1H-pyrrol-2-yl)azetidine-1-carboxylate

생성물 1

HCID 58529502Benzyl 3-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)azetidine-1-carboxylate수율 40%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A solution of benzyl 3-(1-amino-5-cyano-1H-pyrrol-2-yl)azetidine-1-carboxylate (575 mg, 1.94 mmoL) and formamidine acetate (2.02 g, 19.4 mmol) in 1-butanol (8 mL) was stirred at 120° C. for 4 hours. The mixture was then cooled to rt and was partitioned between EtOAc (25 mL) and H2O (25 mL). The layers were separated and the aqueous layer was further extracted with EtOAc (2×25 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated. The crude material was purified by ISCO® chromatography using 3:1 ethyl acetate/hexanes to obtain 250 mg (40%) of the desired product. ES-MS m/z 324.34 [M+H]+, HPLC RT (min) 2.30.

후처리

  1. customwas partitioned between EtOAc (25 mL) and H2O (25 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with EtOAc (2×25 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by ISCO® chromatography

출처 및 근거

ORD 기록
ord-1a857b3795434ff98ec34a023cf5bada
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431695B2

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