Hydrochloric Acid → HCID 178461412, 화합물

HRID 860898노트

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HRID 860898 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]#[C:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[CH3:18])=[C:6]([NH2:8])[CH:7]=1.Cl.[N:20]([O-])=O.[Na+].[OH2:24]>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([C:9]([OH:24])=[C:10]([CH2:11][CH2:12][N:13]3[CH2:17][CH2:16][CH2:15][C@H:14]3[CH3:18])[N:20]=[N:8]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 962Water2회HCID 23668193Sodium NitriteHCID 671046725-Bromo-2-[4-((2r)-2-methyl-pyrrolidin-1-yl)-but-1-ynyl]-phenylamine

생성물 1

HCID 178461412HCID 178461412, 화합물수율 47%

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온도
0 °C

실험 절차

To a mixture of Example 168C (0.10 g, 0.325 mmol) in 2 mL of water was added 1.5 mL 6 M HCl. The resulting solution was cooled to 0° C. and NaNO2 (0.034 g, 0.488 mmol), dissolved in 1 mL water, was added dropwise. The resulting mixture was stirred for 30 minutes at 0° C. and subsequently heated to 90° C. for one hour. After cooling, contents were filtered and the precipitate was washed with 10 mL water and dried under reduced pressure to provide the product in 47% yield as a brown solid in HCl salt form, which was used without further purification. 1H NMR (CD3OD, 300 MHz) δ 8.10 (d, J=9 Hz, 1H), 7.82 (d, J=3 Hz, 1H), 7.60 (dd, J=3, 9 Hz, 1H), 3.89–3.76 (m, 2H), 3.58–3.53 (m, 1H) 3.42–3.23 (m, 4H), 2.38–2.30 (m, 1H), 2.16–2.06 (m, 2H), 1.83–1.75 (m, 1H), 1.51 (d, J=6 Hz, 3H). MS (ESI) [M]+ at 336.

후처리

  1. additionwas added dropwise
  2. temperaturesubsequently heated to 90° C. for one hour
  3. temperatureAfter cooling
  4. filtrationcontents were filtered
  5. washthe precipitate was washed with 10 mL water
  6. customdried under reduced pressure
  7. customto provide the product in 47% yield as a brown solid in HCl salt form, which
  8. customwas used without further purification

출처 및 근거

ORD 기록
ord-5210a7a94a3945ae86f271c04fc36674
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153889B2

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