Hydrochloric Acid → HCID 67540453、化合物

HRID 1192301ノート

反応式

HRID 1192301 の反応式
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[NH:22][CH:21]=[CH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.Cl.[NH:24]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@@H:25](C(O)=O)[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.O1CCOCC1>[C:40]([O:39][C:37](=[O:38])[NH:24][CH:25]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:15]3[NH:22][CH:21]=[CH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:12][CH2:13]1)([CH3:43])([CH3:41])[CH3:42]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 67539894tert-Butyl 4-(5H-pyrrolo[3,2-d]pyrimidin-4-yl)piperazine-1-carboxylate

生成物 1

HCID 67540453HCID 67540453、化合物収率 44.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 4-(5H-Pyrrolo[3,2-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (43 mg, 0.14 mmol) in DCM (4 mL) was added HCl in Dioxane (4M, 1 mL). The mixture was stirred at room temperature for 4 hours. The solvent was removed and the residue was treated with TEA (2 mL), Boc-D-Phe(4-Cl)—OH (43 mg, 0.14 mmol), HOBT (30 mg, 0.222 mmol) and EDCI (41 mg, 0.214 mmol) in DCM (5 mL). The mixture was stirred at room temperature for 12 hours. The solvent was removed and the residue was subject to chromatography on silica gel to give product {1-(4-chlorobenzyl)-2-oxo-2-[4-(5H-pyrrolo[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester (30 mg, 44%). 1H NMR (CDCl3, 400 Hz) δ 9.85 (s, 1H), 8.48 (s, 1H), 7.37 (s, 1H), 7.25-7.23 (d, J=8.4 Hz, 2H), 7.13-7.11 (d, J=8.4 Hz, 2H), 6.60 (s, 1H), 5.39-5.37 (d, J=8.8 Hz, 1H), 4.83-4.78 (m, 1H), 3.81-3.43 (m, 7H), 3.31-3.27 (m, 1H), 3.00-2.91 (m, 2H), 1.41 (s, 9H). MS (ESI+) [M+H]+ 485.

後処理

  1. customThe solvent was removed
  2. stirringThe mixture was stirred at room temperature for 12 hours
  3. customThe solvent was removed

出典と根拠

ORDレコード
ord-93f4fea7be6143b3b11c1a870af0d202
出典データセット
uspto-grants-2014_03
特許番号
US08680114B2

反応ノート

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