Hydrochloric Acid → HCID 10143150、化合物

HRID 2414826ノート

反応式

HRID 2414826 の反応式
C(O[C:6](=[O:32])[NH:7][CH2:8][CH2:9][N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:20][CH3:21])[CH:16]=2)[CH:11]1[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)(C)(C)C.Cl.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:46][C:47]1[C:56]2[C:51](=[N:52][C:53]([CH3:57])=[CH:54][CH:55]=2)[N:50]=[CH:49][CH:48]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CC(O)=O.O>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH:11]2[C:12]3[C:17](=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)[CH2:18][CH2:19][N:10]2[CH2:9][CH2:8][NH:7][C:6]([NH:46][C:47]2[C:56]3[C:51](=[N:52][C:53]([CH3:57])=[CH:54][CH:55]=3)[N:50]=[CH:49][CH:48]=2)=[O:32])=[CH:26][CH:27]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 2724254Sodium bis(trimethylsilyl)amideHCID 124552017-Methyl-[1,8]naphthyridin-4-ylamineHCID 69763736{2-[1-(4-fluoro-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-ethyl}-carbamic acid tert-butyl ester

生成物 1

HCID 10143150HCID 10143150、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

To a stirred solution of {2-[1-(4-fluoro-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-ethyl}-carbamic acid tert-butyl ester (example 106.1, 0.22 g, 0.5 mmol) in glacial AcOH (1 mL) is added conc. HCl (0.1 mL). After 5 min, the reaction mixture is partitioned with CHCl3 (20 mL) and 1 N NaOH (15 mL). The organic phase is evaporated. The residue is taken up in DMSO (2 mL) and treated with CDI (0.2 g, 0.6 mmol, 1.2 eq). The reaction mixture is stirred at rt for 3 h, and then 4-amino-7-methyl-[1,8]-naphthyridine (example C5, 0.19 g, 0.6 mmol) is added. To the resulting solution is added in a single portion NaHMDS (2 M in THF, 1.25 mL, 2.5 mmol). The reaction mixture is stirred at rt for 30 min, then H2O (0.4 mL) is added. The reaction mixture is evaporated and the residue purified by preparative HPLC to provide the title compound.

後処理

  1. customthe reaction mixture is partitioned with CHCl3 (20 mL) and 1 N NaOH (15 mL)
  2. customThe organic phase is evaporated
  3. stirringThe reaction mixture is stirred at rt for 30 min
  4. customThe reaction mixture is evaporated
  5. customthe residue purified by preparative HPLC

出典と根拠

ORDレコード
ord-0ff791c0f9cb4120988598d97de24975
出典データセット
uspto-grants-2004_11
特許番号
US06815451B2

反応ノート

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