Potassium Carbonate → HCID 86616698, 화합물

HRID 597926노트

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HRID 597926 반응식
[CH3:1][CH:2]1[CH2:8][N:7]([C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH2:6][CH2:5][C:4]2[N:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:3]1=2.C([O-])([O-])=O.[K+].[K+].Cl[C:27](C(O[Na])=O)([F:29])[F:28].C([O-])(O)=O.[Na+]>CCOC(C)=O.CN(C=O)C>[F:28][CH:27]([F:29])[O:19][C:16]1[CH:17]=[CH:18][C:3]2[CH:2]([CH3:1])[CH2:8][N:7]([C:9](=[O:14])[C:10]([F:13])([F:11])[F:12])[CH2:6][CH2:5][C:4]=2[N:15]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 178430708HCID 178430708, 화합물HCID 178526069HCID 178526069, 화합물

생성물 1

HCID 86616698HCID 86616698, 화합물수율 54%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

To a mixture of 5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-2-ol (77.0 mg, 281 μmol), K2CO3 (19.0 mg, 141 μmol) and DMF (1.4 ml) was added F2ClCCO2Na (47.0 mg, 310 μmol). The mixture was heated at 90° C. for 2 h. The reaction mixture was parted between sat. aq. NaHCO3 and EtOAc. The organic layer was dried, concentrated in vacuo and purified by means of column chromatography to give 49.0 mg (54%) of 2-(difluoromethoxy)-5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine. MS (ESI) m/z 325.2. A mixture of 2-(difluoromethoxy)-5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine (28.0 mg, 86.0 μmol), K2CO3 (30 mg), MeOH (1 ml) and H2O (200 μl) was heated to reflux for 10 min. The reaction mixture was concentrated in vacuo and the resulting residue was purified by column chromatography to yield 7.0 mg (36%) of 2-(difluoromethoxy)-5-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine. 1H-NMR (CDCl3) δ 7.46 (d, 1H), 6.66 (d, 1H), 3.09 (m, 2H), 3.40-2.90 (m, 4H), 2.74, (dd, 1H), 1.31 (d, 3H) ppm.

후처리

  1. customThe organic layer was dried
  2. concentrationconcentrated in vacuo
  3. custompurified by means of column chromatography

출처 및 근거

ORD 기록
ord-700c18d62c074b448f34ea12acee2507
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897595B2

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