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Cesium carbonate → tert-butyl (3R)-3-[[6-methoxy-5-(5-methyl-1,3-benzothiazol-2-yl)-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate

HRID 1507528
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인쇄 미리보기

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HRID 1507528 반응식
[CH3:1][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>[CH3:19][O:18][C:17]1[N:16]=[C:15]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:14]=[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)[C:12]=1[C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=2[N:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 143445645-Methyl-1,3-benzothiazoleHCID 89554305(R)-Tert-butyl 3-(5-iodo-6-methoxy-2-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylate

생성물 1

HCID 117683808tert-butyl (3R)-3-[[6-methoxy-5-(5-methyl-1,3-benzothiazol-2-yl)-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate

시약·촉매·용매 3

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

실험 절차

Following the same procedure as in step 3 of Example 337 using 5-methyl-1,3-benzothiazole (52.2 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 (0.37 g, 6.00 equiv), Pd(PPh3)4 (40.4 mg, 0.03 mmol, 0.18 equiv) and copper (I) iodide (6.7 mg, 0.09 mmol, 0.18 equiv) in DMF (6 mL). The crude product was purified by chromatography on a silica gel column eluting with petroleum ether/ethyl acetate (15:1-3:1) to afford the title compound as a light yellow solid. MS m/z [M+H]+ (ESI): 541.

후처리

  1. customThe crude product was purified by chromatography on a silica gel column
  2. washeluting with petroleum ether/ethyl acetate (15:1-3:1)

출처 및 근거

ORD 기록
ord-6d98038da51c483aa7e123791fa485f0
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221809B2

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