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

HRID 1363611노트

반응식

HRID 1363611 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-067cd888c5ee4d469f3a6ff95416ee8f
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884207B2

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