4-Methylmorpholine → HCID 22736990, 화합물

HRID 51893

반응식

HRID 51893 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[CH3:42][O:43][C:44]1[C:49]2[N:50]=[C:51]([NH2:53])[S:52][C:48]=2[C:47]([N:54]([CH3:62])[CH2:55][CH:56]2[CH2:61][CH2:60][O:59][CH2:58][CH2:57]2)=[CH:46][CH:45]=1>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([NH:53][C:51]1[S:52][C:48]2[C:47]([N:54]([CH3:62])[CH2:55][CH:56]3[CH2:61][CH2:60][O:59][CH2:58][CH2:57]3)=[CH:46][CH:45]=[C:44]([O:43][CH3:42])[C:49]=2[N:50]=1)=[O:7]

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 2227012-Bromoisonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 227370054-methoxy-N7-methyl-N7-(tetrahydro-pyran-4-ylmethyl)-benzothiazole-2,7-diamine

생성물 1

HCID 22736990HCID 22736990, 화합물수율 14.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 99 mg (0.49 mmol) 2-bromo-isonicotinic acid in 3 ml THF were added 195 mg (0.51 mmol) HATU and 0.11 ml (0.98 mmol) N-methylmorpholine and stirring continued at 30° C. for 5 h. 75 mg (0.24 mmol) 4-methoxy-N7-methyl-N7-(tetrahydro-pyran-4-ylmethyl)-benzothiazole-2,7-diamine was then added and stirring continued at 40° C. for 16 h. The reaction mixture was then diluted with ethyl acetate and washed sequentially with 0.5 N hydrochloric acid, saturated sodium bicarbonate solution and brine. The organic phase was dried over sodium sulfate and concentrated in vactio. Flash chromatography (methanol/dichloromethane) followed by trituration in ether/hexane afforded 17 mg (14%) 2-bromo-N-{4-methoxy-7-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino)-benzothiazol-2-yl}-isonicotinamide as a white crystalline solid. ES-MS m/e (%): 493 (M{81Br}+H+, 100), 491 (M{79Br}+H+, 95).

후처리

  1. stirringstirring
  2. waitcontinued at 40° C. for 16 h
  3. washwashed sequentially with 0.5 N hydrochloric acid, saturated sodium bicarbonate solution and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated in vactio

출처 및 근거

ORD 기록
ord-391745517a374086a4c491907747c53e
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713499B2

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