Chloroform → HCID 68597487、化合物

HRID 1943229ノート

反応式

HRID 1943229 の反応式
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]2[N:19]3[C:20]4[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=4[N:16]=[CH:17][C:18]3=[O:21])[CH2:10]2)[CH2:4][CH2:3]1.[O:23]1[C:27]2=[CH:28][N:29]=[C:30]([CH:32]=O)[CH:31]=[C:26]2[CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+].C(Cl)(Cl)[Cl:54]>CO.CO.C(Cl)Cl>[ClH:54].[O:23]1[C:27]2=[CH:28][N:29]=[C:30]([CH2:32][NH:1][CH:2]3[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]4[N:19]5[C:20]6[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=6[N:16]=[CH:17][C:18]5=[O:21])[CH2:10]4)[CH2:4][CH2:3]3)[CH:31]=[C:26]2[CH2:25][CH2:24]1

参加物

8

反応物 5

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 574231162,3-Dihydrofuro[2,3-c]pyridine-5-carbaldehydeHCID 58200877(2R)-2-[(4-Amino-1-piperidinyl)methyl]-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione

生成物 1

HCID 68597487HCID 68597487、化合物収率 76%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

A suspension of (2R)-2-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione (for a preparation see Example 16A(j)) (70 mg, 0.232 mmol) and 2,3-dihydrofuro[2,3-c]pyridine-5-carbaldehyde (for a synthesis see WO2007122258, Example 43(f) (34.6 mg, 0.232 mmol) in chloroform (5 ml) and methanol (0.250 ml) at room temperature under nitrogen was stirred for 0.5 h (the suspension turned into a solution). Sodium triacetoxyborohydride (155 mg, 0.697 mmol) was then added and the reaction was stirred at room temperature. After 3 h there was no starting material left so a saturated aqueous solution of sodium bicarbonate (25 mL) was added followed by 20% methanol/DCM (25 mL) and the aqueous layer was extracted and then separated from the organic layer. The aqueous layer was extracted again twice with 20% methanol/DCM (2×25 mL). The combined organic extracts were dried on sodium sulphate, filtered and evaporated to afford 90 mg of crude product. The crude product was purified by silica chromatography (0-20% MeOH/DCM) to afford the free base of the title compound as a pale yellow solid (77 mg, 76%).

後処理

  1. customat room temperature
  2. stirringthe reaction was stirred at room temperature
  3. waitAfter 3 h there was
  4. additionwas added
  5. extractionthe aqueous layer was extracted
  6. customseparated from the organic layer
  7. extractionThe aqueous layer was extracted again twice with 20% methanol/DCM (2×25 mL)
  8. customThe combined organic extracts were dried on sodium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. customto afford 90 mg of crude product
  12. customThe crude product was purified by silica chromatography (0-20% MeOH/DCM)

出典と根拠

ORDレコード
ord-69b53732705d483681d34bc884372877
出典データセット
uspto-grants-2013_03
特許番号
US08389524B2

反応ノート

読み込み中…