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

HRID 1366638노트

반응식

HRID 1366638 반응식
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:10][C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[CH3:9])[C:5]([F:16])=[C:4]([NH:17][NH2:18])[N:3]=1.[CH:19]1([CH2:24][C@H:25]([CH2:29][N:30]([CH:38]=[O:39])[O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[C:26](O)=[O:27])[CH2:23][CH2:22][CH2:21][CH2:20]1.CN1CCOCC1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:17][NH:18][C:26](=[O:27])[C@H:25]([CH2:24][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:29][N:30]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH:38]=[O:39])[C:5]([F:16])=[C:6]([N:8]([CH2:10][C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[CH3:9])[N:7]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 57937086(2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acidHCID 86637017HCID 86637017, 화합물

생성물 1

HCID 86637018[(2R)-3-(2-{2-chloro-5-fluoro-6-[(2-furanylmethyl)(methyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide수율 77.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-Chloro-5-fluoro-N-(2-furanylmethyl)-6-hydrazino-N-methyl-4-pyrimidinamine (0.400 g) and (2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acid (0.764 g, 1.770 mmol) were dissolved in DMF. NMM (0.65 mL, 5.912 mmol) was added, followed by HOAt (0.241 g, 1.772 mmol) and EDC (0.3396 g, 1.771 mmol). After stirring overnight, the reaction mixture was purified by RP-HPLC to provide [(2R)-3-(2-{2-chloro-5-fluoro-6-[(2-furanylmethyl)(methyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide as an orange solid (0.6318 g). LCMS: (M+H)+=553.2.

후처리

  1. customthe reaction mixture was purified by RP-HPLC

출처 및 근거

ORD 기록
ord-467f19747fef4cf8bac0496da16bdffd
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

반응 노트

불러오는 중…