Dimethylformamide → 5-Bromo-N-cyclopropylpyridine-2-carboxamide

HRID 557882

반응식

HRID 557882 반응식
C([N:4](CC)[CH:5]([CH3:7])[CH3:6])(C)C.[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([OH:19])=O)=[N:15][CH:16]=1.C1(N)CC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN(C)C=O>C(OCC)(=O)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([NH:4][CH:5]2[CH2:7][CH2:6]2)=[O:19])=[N:15][CH:16]=1

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6085445-Bromopyridine-2-carboxylic acid

생성물 1

HCID 263700895-Bromo-N-cyclopropylpyridine-2-carboxamide

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

N,N-Diisopropylethylamine (0.69 mL, 0.0040 mol) was added to a mixture of 5-bromopyridine-2-carboxylic acid (400 mg, 0.002 mol), cyclopropylamine (0.16 mL, 0.0024 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.1 g, 0.0024 mol) in N,N-dimethylformamide (9.4 mL, 0.12 mol) at 0° C. and the mixture was stirred overnight at room temperature. The mixture was diluted with ethyl acetate, washed with water and brine successively, dried over sodium sulfate, filtered and concentrated. The product was purified by CombiFlash eluting with CH2Cl2/EtOAc (max.EtOAc 20%). LC-MS: 241.1/243.1 (M+H+)

후처리

  1. washwashed with water and brine successively
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by CombiFlash
  6. washeluting with CH2Cl2/EtOAc (max.EtOAc 20%)

출처 및 근거

ORD 기록
ord-608f3976613242cc85a4cb23aedc7b10
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058288B2

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