Diisopropylethylamine → HCID 59200049, 화합물

HRID 2382107노트

반응식

HRID 2382107 반응식
[CH3:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([NH2:11])[CH:3]=1.[F:12][C:13]1[CH:14]=[C:15]([C:19]2[N:24]=[C:23]([CH3:25])[C:22]([C:26](O)=[O:27])=[CH:21][N:20]=2)[CH:16]=[CH:17][CH:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[CH3:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([NH:11][C:26]([C:22]2[C:23]([CH3:25])=[N:24][C:19]([C:15]3[CH:16]=[CH:17][CH:18]=[C:13]([F:12])[CH:14]=3)=[N:20][CH:21]=2)=[O:27])[CH:3]=1

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 617025872-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acidHCID 68552172HCID 68552172, 화합물

생성물 1

HCID 59200049HCID 59200049, 화합물수율 36%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-methyl-pyrrolo[3,2-c]pyridin-1-ylamine (224 mg, 1.52 mmol), 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (354 mg, 1.52 mmol), HATU (693 mg, 1.82 mmol) and DIPEA (593 mg, 4.59 mmol) in DMF (8 mL) is heated at 1500 C. for 1 h. The reaction is quenched with water, NaHCO3 (168 mg, 2 mmol) is added and the mixture is extracted with EtOAc. The organic layer is separated, dried (Na2SO4), filtered and concentrated. The residue is first purified by silica gel column chromatography eluting with 10% MeOH in DCM and then recrystallized from EtOAc to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-c]pyridin-1-yl)-amide (198 mg). MS: 362 (M+H); 1H NMR (300 MHz, CD3OD): δ 9.12 (s, 1H), 8.86 (s, 1H), 8.35 (d, 1H), 8.15-8.31 (m, 2H), 7.47-7.60 (m, 2H), 7.35 (s, 1H), 7.29 (t, 1H), 2.84 (s, 3H), 2.44 (s, 3H).

후처리

  1. temperatureis heated at 1500 C
  2. additionis added
  3. extractionthe mixture is extracted with EtOAc
  4. customThe organic layer is separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is first purified by silica gel column chromatography
  9. washeluting with 10% MeOH in DCM
  10. customrecrystallized from EtOAc

출처 및 근거

ORD 기록
ord-63f22b8dbdc04c0786c484fa6467207c
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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