Triethylamine → HCID 178434276、化合物

HRID 537194ノート

反応式

HRID 537194 の反応式
Cl.C([N:6]1[CH:14]=[C:13]2[C:8]([C:9](=[O:22])[NH:10][C:11]3([CH2:20][CH:19]4[NH:21][CH:16](CC4)[CH2:15]3)[CH2:12]2)=[N:7]1)(C)(C)C.[CH3:23][C:24]1[C:32]2[C:27](=[C:28]([CH3:36])[CH:29]=[C:30]([C:33]([OH:35])=O)[CH:31]=2)[NH:26][N:25]=1.C(N(CC)CC)C.[CH3:44][CH2:45][CH2:46]P1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:23][C:24]1[C:32]2[C:27](=[C:28]([CH3:36])[CH:29]=[C:30]([C:33]([N:21]3[CH2:16][CH2:15][C:11]4([NH:10][C:9](=[O:22])[C:8]5[N:7]([CH:45]([CH3:46])[CH3:44])[N:6]=[CH:14][C:13]=5[CH2:12]4)[CH2:20][CH2:19]3)=[O:35])[CH:31]=2)[NH:26][N:25]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 674914372'-tert-butyl-4',6'-dihydro-8-azaspiro[bicyclo[3.2.1]octane-3,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one hydrochloride2 回HCID 178434277HCID 178434277、化合物

生成物 1

HCID 178434276HCID 178434276、化合物収率 25.2%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1′-isopropyl-4′,6′-dihydrospiro[piperidine-4,5′-pyrazolo[3,4-c]pyridin]-7′(1H)-one hydrochloride salt (Intermediate 2, 430 mg, 1.3 mmol) and 3,7-dimethyl-1H-indazole-5-carboxylic acid (306 mg, 1.6 mmol) in dimethylformamide (2 mL) was added triethylamine (0.75 mL, 5.4 mmol), 4-dimethylaminopyridine (33 mg, 0.37 mmol), and 1-propanephosphonic acid cyclic anhydride (0.52 mL, 1.74 mmol, 50% solution in ethyl acetate), and the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered, and concentrated to a solid. The solid was purified via flash column chromatography (0-15% methanol/dichloromethane) to afford a glassy solid. The glassy solid was stirred in ethyl acetate for 16 hours and the resulting solid collected by vacuum filtration to afford the desired product as a white solid (138 mg). +ESI (M+H) 421.0; 1H NMR (400 MHz, CD3OD, δ): 7.65 (s, 1H) 7.42 (s, 1H) 7.21 (s, 1H) 5.50 (m, 1H) 3.95 (br. s., 1H) 3.50-3.62 (br. s., 3H) 2.97 (s, 2H) 2.56 (m, 6H) 1.83 (br. s., 4H) 1.44 (d, 6H).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a solid
  6. customThe solid was purified via flash column chromatography (0-15% methanol/dichloromethane)
  7. customto afford a glassy solid
  8. filtrationthe resulting solid collected by vacuum filtration

出典と根拠

ORDレコード
ord-15ce9741487f4c8a8eaea116690541e8
出典データセット
uspto-grants-2014_10
特許番号
US08859773B2

反応ノート

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