Sodium Bicarbonate → HCID 56599062、化合物

HRID 1035260ノート

反応式

HRID 1035260 の反応式
[C:1]1([C:7]2[O:11][C:10]([C:12]([N:14]3[CH2:17][CH:16]([O:18][C:19]4[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=4)[CH2:15]3)=[O:13])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:28][C:29]1([OH:36])[CH2:35][CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[Na].C([O-])(O)=O.[Na+]>ClCCl>[OH:36][C:29]1([CH3:28])[CH2:35][CH2:34][CH2:33][N:32]([CH2:23][C:22]2[CH:21]=[CH:20][C:19]([O:18][CH:16]3[CH2:15][N:14]([C:12]([C:10]4[O:11][C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[N:8][N:9]=4)=[O:13])[CH2:17]3)=[CH:26][CH:25]=2)[CH2:31][CH2:30]1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 58043115HCID 58043115、化合物HCID 666532494-Hydroxy-4-Methyl-Hexahydro-1H-azepine hydrochloride

生成物 1

HCID 56599062HCID 56599062、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Intermediate 71A (0.15 g, 0.43 mmol), (0.098 g, 0.64 mmol) 4-methylazepan-4-ol hydrochloride (0.062 g, 1.15 mmol, see Helvetica Chimica Acta, 45, 1823-32, (1962)) and TEA (0.159 mL, 1.15 mmol) were mixed in dichloromethane (4 mL). The mixture was stirred at RT for 30 min and then sodium triacetoxyhydroborate (0.182 g, 0.86 mmol) was added and the mixture was stirred at RT overnight. Aqueous NaHCO3 (sat., 3 mL) and dichloromethane (3 mL) were added and the mixture was filtered through a phase separator and the solvent was removed by evaporation. The product was purified twice by preparative reverse-phase HPLC at pH 10 to give 53 mg (40%). 1H NMR (600 MHz, DMSO) δ 1.11 (s, 3H), 1.35-1.45 (m, 1H), 1.55-1.74 (m, 5H), 2.32-2.64 (m, 4H), 3.46-3.55 (m, 2H), 4.04-4.16 (m, 1H), 4.52-4.67 (m, 2H), 5.05-5.2 (m, 2H), 6.85 (d, 2H), 7.25 (d, 2H), 7.61-7.73 (m, 3H), 8.05-8.11 (m, 2H), LC purity: 96%.

後処理

  1. stirringthe mixture was stirred at RT overnight
  2. filtrationthe mixture was filtered through a phase separator
  3. customthe solvent was removed by evaporation
  4. customThe product was purified twice by preparative reverse-phase HPLC at pH 10
  5. customto give 53 mg (40%)

出典と根拠

ORDレコード
ord-8b2fda03e47c440aa3ae45ce7b09b5c5
出典データセット
uspto-grants-2013_10
特許番号
US08546375B2

反応ノート

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