Cyclohexylamine → 5-Bromo-N-cyclohexylpyridine-3-carboxamide

HRID 1507087노트

반응식

HRID 1507087 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH:11]1([NH2:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH:17][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:9]

참가 물질

7

반응물 4

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 887075-Bromonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 48000295-Bromo-N-cyclohexylpyridine-3-carboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of 5-bromonicotinic acid (XLII) (500 mg, 2.49 mmol) in DMF (8 mL), was added cyclohexanamine (XLIII) (247 mg, 2.49 mmol) and DIPEA (643 mg, 4.98 mmol). The reaction was cooled at 0° C. before adding HATU (947 mg, 2.49 mmol). The reaction was warmed to room temperature and stirred for 4 hrs. The reaction was diluted with EtOAc, washed with 2× water, brine, dried over MgSO4 and concentrated under vacuum to yield crude 5-bromo-N-cyclohexylnicotinamide (XLIV). The product was used without further purification. ESIMS found for C12H15BrN2O m/z 283 (M+H).

후처리

  1. temperatureThe reaction was warmed to room temperature
  2. washwashed with 2× water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-11cb45297b464db5a4fbaba57ca8867e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221793B2

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