Diisopropylethylamine → 1-tert-butyl-8-(methylsulfanyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 45799

反応式

HRID 45799 の反応式
[C:1]([N:5]1[C:17]2[C:16]3[N:15]=[C:14]([S:18][CH3:19])[N:13]=[CH:12][C:11]=3[CH:10]=[CH:9][C:8]=2[C:7]([C:20]([OH:22])=O)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[O:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[O:29][NH2:30].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[C:1]([N:5]1[C:17]2[C:16]3[N:15]=[C:14]([S:18][CH3:19])[N:13]=[CH:12][C:11]=3[CH:10]=[CH:9][C:8]=2[C:7]([C:20]([NH:30][O:29][CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][O:23]2)=[O:22])=[N:6]1)([CH3:2])([CH3:3])[CH3:4]

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 679769231-tert-butyl-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid

生成物 1

HCID 866683921-tert-butyl-8-(methylsulfanyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide収率 50%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

1-tert-butyl-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid 40 mg (0.112 mmol) was reacted in dry DMF (2 ml) with O-(tetrahydro-2H-pyran-2-yl)hydroxylamine 25 mg (0.21 mmol), TBTU 70 mg (0.21 mmol) and DIPEA 0.110 ml (1.19 mmol) at room temperature for 3 hours. The reaction was worked up with water, saturated NaHCO3 and extracted with ethyl acetate. The organic phase, dried on Na2SO4, filtered and evaporated, was purified on silica with DCM/EtOAc 7/3 to give 23 mg (50%) of 1-tert-butyl-8-(methylsulfanyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide. LC/MS (m/z): 416.1 [M+H]+, HPLC (254 nm) method 3 Rt 6.94 min.

後処理

  1. extractionextracted with ethyl acetate
  2. customThe organic phase, dried on Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customwas purified on silica with DCM/EtOAc 7/3

出典と根拠

ORDレコード
ord-9fb976c30e2541bd8939abe6bf1a5a41
出典データセット
uspto-grants-2013_09
特許番号
US08541576B2

関連ノート

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