Trifluoroacetic acid → Ethyl 8-(1-acetyl-piperidin-4-yl)amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

HRID 44596

반응식

HRID 44596 반응식
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.[C:21]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)(=[O:23])[CH3:22].C(O)(C(F)(F)F)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>CN(C)C=O>[C:21]([N:24]1[CH2:29][CH2:28][CH:27]([NH:1][C:2]2[N:11]=[CH:10][C:9]3[CH2:8][CH2:7][C:6]4[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=4[C:4]=3[N:3]=2)[CH2:26][CH2:25]1)(=[O:23])[CH3:22]

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 122563N-Acetyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydrideHCID 24993827ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

생성물 1

HCID 45141159Ethyl 8-(1-acetyl-piperidin-4-yl)amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate수율 70%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 5.187 g (19 mmol) of ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate in dry dimethylformamide (120 mL), were added 1-acetyl-4-piperidone (4.7 mL, 38 mmol), CF3COOH (10 mL, 128 mmol) and NaBH(OAc)3 (8.862 g, 42 mmol). After 18 hours, NaOH 0.33N (800 mL, 264 mmol) was added dropwise to the mixture. The precipitate was filtered, washed with water and dried in oven to dryness to give 5.3 g (70% yield) of the title compound.

후처리

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried in oven to dryness

출처 및 근거

ORD 기록
ord-061067fb3a22442db40a376ffbe1000a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541429B2

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