Sodium Bicarbonate → HCID 56599062, 화합물

HRID 1035260노트

반응식

HRID 1035260 반응식
[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

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 58043115HCID 58043115, 화합물HCID 666532494-Hydroxy-4-Methyl-Hexahydro-1H-azepine hydrochloride

생성물 1

HCID 56599062HCID 56599062, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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%.

후처리

  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%)

출처 및 근거

ORD 기록
ord-8b2fda03e47c440aa3ae45ce7b09b5c5
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546375B2

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