Dichloromethane → Tert-butyl 4-hydroxy-4-{[(3-nitro[1,5]naphthyridin-4-yl)amino]methyl}piperidine-1-carboxylate

HRID 1363611ノート

反応式

HRID 1363611 の反応式
[NH2:1][CH2:2][C:3]1([OH:16])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.C([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])C.Cl[C:25]1C2C(=NC=CC=2)[N:28]=[CH:27][C:26]=1[N+:35]([O-:37])=[O:36].Cl[CH2:39]Cl>C(=O)(O)[O-].[Na+]>[OH:16][C:3]1([CH2:2][NH:1][C:25]2[C:20]3[C:21](=[CH:39][CH:23]=[CH:22][N:19]=3)[N:28]=[CH:27][C:26]=2[N+:35]([O-:37])=[O:36])[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:7][CH2:8]1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 125432134-Chloro-3-nitronaphthyridineHCID 23396319tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 57515527Tert-butyl 4-hydroxy-4-{[(3-nitro[1,5]naphthyridin-4-yl)amino]methyl}piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

実験手順

Under a nitrogen atmosphere a solution of tert-butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate (38.9 g, 169 mmol, prepared according to Parts A and B of Example 4) in dichloromethane (420 mL) was cooled to 0° C. Triethylamine (23.6 mL, 169 mmol) was added followed by the portionwise addition of 4-chloro-3-nitronaphthyridine (30.8 g, 147 mmol). The reaction mixture was stirred at ambient temperature overnight and then diluted with saturated aqueous sodium bicarbonate (200 mL). The layers were separated and the aqueous was extracted with dichloromethane (3×100 mL). The combined organics were concentrated under reduced pressure to provide a dark yellow solid. This material was triturated with saturated aqueous sodium bicarbonate, isolated by filtration, rinsed well with water, and then dried in a vacuum oven at 70° C. overnight to provide 58.85 g of tert-butyl 4-hydroxy-4-{[(3-nitro[1,5]naphthyridin-4-yl)amino]methyl}piperidine-1-carboxylate as a yellow solid.

後処理

  1. customThe layers were separated
  2. extractionthe aqueous was extracted with dichloromethane (3×100 mL)
  3. concentrationThe combined organics were concentrated under reduced pressure
  4. customto provide a dark yellow solid
  5. customThis material was triturated with saturated aqueous sodium bicarbonate
  6. customisolated by filtration
  7. washrinsed well with water
  8. customdried in a vacuum oven at 70° C. overnight

出典と根拠

ORDレコード
ord-067cd888c5ee4d469f3a6ff95416ee8f
出典データセット
uspto-grants-2011_02
特許番号
US07884207B2

反応ノート

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