1,2-Dichloroethane → ((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-2-methyl-6-(1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide

HRID 1366387노트

반응식

HRID 1366387 반응식
[F:1][C:2]1[C:3]([NH:14][NH2:15])=[N:4][C:5]([CH3:13])=[N:6][C:7]=1[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[CH:16]1([CH2:21][C@H:22]([CH2:26][N:27]([CH:36]=[O:37])[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:23](O)=[O:24])[CH2:20][CH2:19][CH2:18][CH2:17]1.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C>[CH:16]1([CH2:21][C@@H:22]([C:23]([NH:15][NH:14][C:3]2[C:2]([F:1])=[C:7]([N:8]3[CH2:12][CH2:11][CH2:10][CH2:9]3)[N:6]=[C:5]([CH3:13])[N:4]=2)=[O:24])[CH2:26][N:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:36]=[O:37])[CH2:20][CH2:19][CH2:18][CH2:17]1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 21305218(R)-3-(Benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acidHCID 669360205-Fluoro-4-hydrazino-2-methyl-6-(1-pyrrolidinyl)pyrimidine

생성물 1

HCID 86636916((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-2-methyl-6-(1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide수율 55%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-Fluoro-4-hydrazino-2-methyl-6-(1-pyrrolidinyl)pyrimidine (69 mg, 0.33 mmol), (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (110 mg, 0.36 mmol), and HOAt (49 mg, 0.36 mmol) were dissolved in 2 mL of DMF. NMM (0.18 mL, 1.65 mmol) was added, followed by EDC (69 mg, 0.36 mmol). After stirring overnight at room temperature, the reaction mixture was purified by RP-HPLC to provide ((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-2-methyl-6-(1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide (90 mg, 55%).

후처리

  1. customthe reaction mixture was purified by RP-HPLC

출처 및 근거

ORD 기록
ord-e4acb731eb85483682ff3d4b81845221
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

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