Triethylamine → N-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N'-(4-pyrimidinyl)urea

HRID 2084348노트

반응식

HRID 2084348 반응식
[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]3[C@@H:12](C(O)=O)[C@H:7]3[C:6]=2[C:5]([F:16])=[CH:4][CH:3]=1.C([N:19]([CH2:22][CH3:23])[CH2:20]C)C.[NH2:24][C:25]1C=C[N:28]=[CH:27][N:26]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]3[C@@H:12]([NH:24][C:25]([NH:26][C:27]4[CH:23]=[CH:22][N:19]=[CH:20][N:28]=4)=[O:38])[C@H:7]3[C:6]=2[C:5]([F:16])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 689584-AminopyrimidineHCID 199401P,P-Diphenylphosphinic azideHCID 21304923(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid

생성물 1

HCID 60077559N-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N'-(4-pyrimidinyl)urea

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
110 °C

실험 절차

(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid (50 mg, 0.22 mmol, ee˜90%) was mixed with toluene (1 ml), triethylamine (0.034 ml, 1.1 eq), 4-aminopyrimidine (25 mg, 1.1 eq), DPPA (0.054 ml, 1.1 eq). The reaction mixture was then heated with stirring at 110° C. for 3 h. The reaction mixture was concentrated by rotary evaporation and the product was crystallized from ethanol and collected by filtration to give 20 mg of the product as white solid.

후처리

  1. temperatureThe reaction mixture was then heated
  2. concentrationThe reaction mixture was concentrated by rotary evaporation
  3. customthe product was crystallized from ethanol
  4. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-97bb1be96e7145c389859ae625720692
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716850B2

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