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 1366706ノート

反応式

HRID 1366706 の反応式
[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

参加物

7

反応物 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

生成物 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)formamide収率 57.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(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.

後処理

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

出典と根拠

ORDレコード
ord-1d548743e8df445bac8807cef43788fb
出典データセット
uspto-grants-2011_02
特許番号
US07893056B2

反応ノート

読み込み中…