Hydrochloric Acid → 3-(piperidin-4-yl)-4,5-dihydro-1H-pyrido[3,2-d][1,3]diazepin-2(3H)-one dihydrochloride

HRID 2378966ノート

反応式

HRID 2378966 の反応式
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[CH2:5][CH2:4][N:3]1[CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1.FC(F)(F)C(O)=O.[ClH:33].C(OCC)C>ClCCl>[ClH:33].[ClH:33].[NH:16]1[CH2:17][CH2:18][CH:13]([N:3]2[CH2:4][CH2:5][C:6]3[N:12]=[CH:11][CH:10]=[CH:9][C:7]=3[NH:8][C:2]2=[O:1])[CH2:14][CH2:15]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 59006380Tert-butyl 4-(2-oxo-1,2,4,5-tetrahydropyrido[3,2-d][1,3]diazepin-3-yl)piperidine-1-carboxylate

生成物 1

HCID 693141183-(piperidin-4-yl)-4,5-dihydro-1H-pyrido[3,2-d][1,3]diazepin-2(3H)-one dihydrochloride収率 88%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

tert-Butyl 4-(2-oxo-4,5-dihydro-1H-pyrido[3,2-d][1,3]diazepin-3(2H)-yl)piperidine-1-carboxylate (0.814 g, 2.350 mmol) was dissolved in dichloromethane (8.0 ml). Trifluoroacetic acid (2.0 ml, 26.0 mmol) was added to the mixture at room temperature. The mixture was stirred at room temperature for 4 hours. All volatiles were removed and the residue was dissolved in dichloromethane (10 mL). 2M Hydrogen chloride in diethyl ether (4.11 ml, 8.22 mmol) was added to the mixture. The reaction was stirred at room temperature for 15 minutes and all volatiles were removed. The resulting off-white solid was washed 4 times with anhydrous diethyl ether. Title compound was obtained as white solid in 88% yield. 1H NMR (500 MHz, D2O) δ ppm 8.28 (d, J=4.88 Hz, 1 H) 8.05 (d, J=8.24 Hz, 1 H) 7.74-7.82 (m, 1 H) 4.30-4.41 (m, 1 H) 3.71-3.78 (m, 2 H) 3.51-3.62 (m, 2 H) 3.34-3.41 (m, 2 H) 3.09-3.20 (m, 2 H) 1.98-2.14 (m, 4 H).

後処理

  1. customAll volatiles were removed
  2. dissolutionthe residue was dissolved in dichloromethane (10 mL)
  3. stirringThe reaction was stirred at room temperature for 15 minutes
  4. customall volatiles were removed
  5. washThe resulting off-white solid was washed 4 times with anhydrous diethyl ether

出典と根拠

ORDレコード
ord-97a2ff73dbe346b7be636963db47d0c7
出典データセット
uspto-grants-2008_12
特許番号
US07470680B2

反応ノート

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