Diisopropylethylamine → {1-[3-(5,6,7,8-Tetrahydro-[1,8]-naphthyridin-2-ylmethyl)-pyrrolidine-1-carbonyl]-piperidin-4-yl}-acetic acid ethyl ester

HRID 277888ノート

反応式

HRID 277888 の反応式
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.ClC(Cl)(O[C:27](=[O:33])OC(Cl)(Cl)Cl)Cl.[N:35]1[C:44]2[NH:43][CH2:42][CH2:41][CH2:40][C:39]=2[CH:38]=[CH:37][C:36]=1[CH2:45][CH:46]1[CH2:50][CH2:49][NH:48][CH2:47]1>CC#N.CN(C=O)C>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][CH:5]1[CH2:6][CH2:7][N:2]([C:27]([N:48]2[CH2:49][CH2:50][CH:46]([CH2:45][C:36]3[CH:37]=[CH:38][C:39]4[CH2:40][CH2:41][CH2:42][NH:43][C:44]=4[N:35]=3)[CH2:47]2)=[O:33])[CH2:3][CH2:4]1)[CH3:13]

参加物

7

反応物 4

HCID 81531Diisopropylethylamine2 回HCID 94429TriphosgeneHCID 120171643-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-ylmethyl)-pyrrolidineHCID 45358839Piperidin-4-yl-acetic acid ethyl ester hydrochloride

生成物 1

HCID 70160755{1-[3-(5,6,7,8-Tetrahydro-[1,8]-naphthyridin-2-ylmethyl)-pyrrolidine-1-carbonyl]-piperidin-4-yl}-acetic acid ethyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒2 回

実験手順

To a solution of 6-2 (31 mg, 0.15 mmol), DIPEA (77 μL, 0.44 mmol), and CH3CN (1.5 mL) at 0° C. was added dropwise a solution of triphosgene (15 mg, 52 mmol) in CH3CN (150 μL). Afer 30 min., a solution of 1-8 (43 mg, 0.15 mmol) and DIPEA (77 μL, 0.44 mmol) in DMF (0.8 mL) was added, followed by removal of the cooling bath. After 16 hrs, the reaction mixture was poured into EtOAc and sat. NaHCO3. The EtOAc portion was then washed with H2O and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 10% ethanol/EtOAc) gave 6-3 as a colorless oil.

後処理

  1. customfollowed by removal of the cooling bath
  2. additionthe reaction mixture was poured into EtOAc and sat. NaHCO3
  3. washThe EtOAc portion was then washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8d616ea15c564bee8b112111b05b7320
出典データセット
uspto-grants-2002_03
特許番号
US06358970B1

反応ノート

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