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Cesium carbonate → HCID 49832654, 화합물

HRID 1947518
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HRID 1947518 반응식
[Na].[N:2]1([CH2:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.Cl[C:20]1[S:21][C:22]2[C:23]([N:28]=1)=[N:24][CH:25]=[CH:26][N:27]=2.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[N:2]1([CH2:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][C:20]4[S:21][C:22]5[C:23]([N:28]=4)=[N:24][CH:25]=[CH:26][N:27]=5)=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1
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반응물 3

HCID 10796Cesium carbonateHCID 574827642-Chloro-[1,3]thiazolo[4,5-b]pyrazineHCID 68771253HCID 68771253, 화합물

생성물 1

HCID 49832654HCID 49832654, 화합물수율 26%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-morpholin-4-ylmethyl-1H-indol-6-ol sodium salt (130 mg, 0.51 mmol) and 2-chloro-thiazolo[4,5-b]pyrazine (70 mg, 0.41 mmol) in DMF (1.4 mL) was added Cs2CO3 (43 mg, 0.12 mmol) and the resulting suspension was stirred (rt, 16 h). The reaction mixture was filtered and the solid was rinsed with EtOAc. The reaction mixture was concentrated in vacuo. The resulting residue was purified via reverse phase HPLC to provide the title compound as a white powder (38.3 mg, 26%). MS (ESI): mass calculated for C18H17N5O2S, 367.1; m/z found, 368.1 [M+H]+. 1H NMR (600 MHz, CDCl3): 8.51 (d, J=2.6, 1H), 8.32 (d, J=2.6, 1H), 8.21 (s, 1H), 7.83 (d, J=8.6, 1H), 7.45 (d, J=2.2, 1H), 7.21 (d, J=2.3, 1H), 7.12 (dd, J=8.6, 2.2, 1H), 3.75-3.69 (m, 6H), 2.51 (s, 4H).

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was rinsed with EtOAc
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe resulting residue was purified via reverse phase HPLC

출처 및 근거

ORD 기록
ord-454000d8d7b54872b7add10f25285fcb
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08399465B2

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