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Cesium carbonate → Tert-butyl 3-(6-methoxy-5-(7-methylbenzo[d]thiazol-2-yl)-2-morpholino-1,6-dihydropyrimidin-4-ylamino)piperidine-1-carboxylate

HRID 1507527
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HRID 1507527 반응식
I[C:2]1[CH:7]([O:8][CH3:9])[NH:6][C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][C:3]=1[NH:16][C@@H:17]1[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1.[CH3:30][C:31]1[C:39]2[S:38][CH:37]=[N:36][C:35]=2[CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.I[Cu]>[CH3:9][O:8][CH:7]1[NH:6][C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][C:3]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]2)=[C:2]1[C:37]1[S:38][C:39]2[C:31]([CH3:30])=[CH:32][CH:33]=[CH:34][C:35]=2[N:36]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 156550227-Methylbenzo[d]thiazoleHCID 178494221tert-butyl (3R)-3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)-1,6-dihydropyrimidin-4-yl]amino]piperidine-1-carboxylate

생성물 1

HCID 178494220Tert-butyl 3-(6-methoxy-5-(7-methylbenzo[d]thiazol-2-yl)-2-morpholino-1,6-dihydropyrimidin-4-ylamino)piperidine-1-carboxylate

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 11979704Tetrakis(triphenylphosphine)palladium촉매
HCID 6228Dimethylformamide용매

실험 절차

Following the same procedure as in step 3 of Example 337 using tert-butyl (3R)-3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)-1,6-dihydropyrimidin-4-yl]amino]piperidine-1-carboxylate (30 mg, 0.06 mmol, 1.00 equiv), 7-methyl-1,3-benzothiazole (15.5 mg, 0.10 mmol, 1.81 equiv), tetrakis(triphenylphosphane) palladium (12 mg, 0.01 mmol, 0.18 equiv), iodocopper (2 mg, 0.01 mmol, 0.18 equiv), and cesium Carbonate (112.8 mg, 0.35 mmol, 6.00 equiv) in N,N-dimethylformamide (2.5 mL). The crude product was purified through a silica gel column with ethyl acetate/petroleum ether (1:10-1:5) to afford the title compound as a brown solid.

후처리

  1. customThe crude product was purified through a silica gel column with ethyl acetate/petroleum ether (1:10-1:5)

출처 및 근거

ORD 기록
ord-2bed66162564450595ec942986e6eece
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221809B2

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