1,2-Dichloroethane → [(2R)-3-(2-{2-chloro-5-fluoro-6-[(4-methyl-1-piperazinyl)(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide

HRID 1366706노트

반응식

HRID 1366706 반응식
[CH2:1]([CH:3]([CH2:20][CH2:21][CH3:22])[CH2:4][C@H:5]([CH2:9][N:10]([CH:18]=[O:19])[O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[C:6]([OH:8])=O)C.[Cl:23][C:24]1[N:29]=[C:28]([N:30]([N:37]2[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]2)[CH2:31][C:32]2[S:33][CH:34]=[CH:35][N:36]=2)[C:27]([F:44])=[C:26]([NH:45][NH2:46])[N:25]=1.CN1CCOCC1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Cl:23][C:24]1[N:25]=[C:26]([NH:45][NH:46][C:6](=[O:8])[C@H:5]([CH2:4][CH:3]2[CH2:1][CH2:22][CH2:21][CH2:20]2)[CH2:9][N:10]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:18]=[O:19])[C:27]([F:44])=[C:28]([N:30]([N:37]2[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]2)[CH2:31][C:32]2[S:33][CH:34]=[CH:35][N:36]=2)[N:29]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 866370322-chloro-5-fluoro-6-hydrazino-N-(4-methyl-1-piperazinyl)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamineHCID 86637034(2R)-4-Ethyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}heptanoic acid

생성물 1

HCID 86637033[(2R)-3-(2-{2-chloro-5-fluoro-6-[(4-methyl-1-piperazinyl)(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide수율 57.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(2R)-4-Ethyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}heptanoic acid (0.3764 g, 1.257 mmol), 2-chloro-5-fluoro-6-hydrazino-N-(4-methyl-1-piperazinyl)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine (0.1683 g), NMM (0.298 mL, 2.71 mmol), HOAt (0.074 g, 0.542 mmol), and EDC (0.104 g, 0.542 mmol) were dissolved in DMF (10 mL). The reaction was left to stir overnight. Purification by RP-HPLC provided [(2R)-3-(2-{2-chloro-5-fluoro-6-[(4-methyl-1-piperazinyl)(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide as a brown oily solid (0.1688 g). LCMS: (M+H)+=655.4.

후처리

  1. waitThe reaction was left
  2. customPurification by RP-HPLC

출처 및 근거

ORD 기록
ord-1d548743e8df445bac8807cef43788fb
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

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