Trifluoroacetic acid → tert-Butyl 4-({3-[(2,6-diethylphenyl)carbamoyl]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazolin-8-yl}amino)piperidine-1-carboxylate

HRID 81951ノート

反応式

HRID 81951 の反応式
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([NH:18][C:19]4[C:24]([CH2:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:20]=4[CH2:27][CH3:28])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.[C:29]([N:36]1[CH2:41][CH2:40][C:39](=O)[CH2:38][CH2:37]1)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(O)(C(F)(F)F)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>CN(C)C=O>[CH2:27]([C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([CH2:25][CH3:26])[C:19]=1[NH:18][C:16]([C:12]1[C:6]2[CH2:7][CH2:8][C:9]3[CH:10]=[N:11][C:2]([NH:1][CH:39]4[CH2:40][CH2:41][N:36]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:37][CH2:38]4)=[N:3][C:4]=3[C:5]=2[N:14]([CH3:15])[N:13]=1)=[O:17])[CH3:28]

参加物

7

反応物 5

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 670756638-Amino-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

生成物 1

HCID 44555919tert-Butyl 4-({3-[(2,6-diethylphenyl)carbamoyl]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazolin-8-yl}amino)piperidine-1-carboxylate収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 8-amino-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1.0 g, 2.66 mmol) in dry dimethylformamide (20 mL), were added 1-Boc-4-piperidone (1.06 g mL, 5.32 mmol), CF3COOH (1.7 mL, 22.7 mmol) and NaBH(OAc)3 (1.12 g, 5.32 mmol). After 20 hours, NaOH 2N (12 mL, 24 mmol) was added dropwise to the mixture. The precipitate was filtered, washed with water and dried. The crude material was purified by flash chromatography on silica gel eluted with dichloromethane/methanol 97:3 to give the 1.2 g of to the pure title compound (80% yield).

後処理

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried
  4. customThe crude material was purified by flash chromatography on silica gel
  5. washeluted with dichloromethane/methanol 97:3

出典と根拠

ORDレコード
ord-1c4f728ea8b24a8e94efc7edc2079012
出典データセット
uspto-grants-2014_09
特許番号
US08846701B2

反応ノート

読み込み中…