Cesium carbonate → HCID 117683816, 화합물

HRID 1507537노트

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HRID 1507537 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1.I[C:12]1[C:13]([NH:26][C@@H:27]2[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]2)=[N:14][C:15]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[N:16][C:17]=1[O:18][CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:12]3[C:13]([NH:26][C@@H:27]4[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]4)=[N:14][C:15]([N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[N:16][C:17]=3[O:18][CH3:19])=[N:7][C:6]=2[CH:10]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 36101555-BromobenzothiazoleHCID 89554305HCID 89554305, 화합물

생성물 1

HCID 117683816HCID 117683816, 화합물

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

Following the same procedure as in step 3 of Example 337 using 5-bromo-1,3-benzothiazole (74.9 mg, 0.35 mmol, 1.80 equiv), tert-butyl (3R)-3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (100.0 mg, 0.19 mmol, 1.00 equiv), cesium carbonate (370 mg, 1.14 mmol, 6.00 equiv), Pd(PPh3)4 (40.4 mg, 0.035 mmol, 0.18 equiv), copper (I) iodide (6.7 mg, 0.035 mmol, 0.18 equiv) in DMF (5.0 mL). The crude product was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (10:1-5:1) to provide the title compound as a light yellow solid. MS m/z [M+H]+ (ESI): 605

후처리

  1. customThe crude product was purified by flash chromatography on silica gel
  2. washeluting with petroleum ether/ethyl acetate (10:1-5:1)

출처 및 근거

ORD 기록
ord-a0fd4fa54616419b82963df0a1e32b31
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221809B2

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