Diisopropylethylamine → (3R)-1-{3-[1-(4-ethylphenyl)-1H-imidazol-5-yl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-N,N-dimethylpyrrolidin-3-amine

HRID 72720

反応式

HRID 72720 の反応式
[CH3:1][N:2]([CH3:8])[C@@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)C(C)C)(C)C.Cl[C:19]1[N:24]=[CH:23][N:22]=[C:21]2[N:25]([CH3:41])[N:26]=[C:27]([C:28]3[N:32]([C:33]4[CH:38]=[CH:37][C:36]([CH2:39][CH3:40])=[CH:35][CH:34]=4)[CH:31]=[N:30][CH:29]=3)[C:20]=12>C(#N)C>[CH2:39]([C:36]1[CH:37]=[CH:38][C:33]([N:32]2[C:28]([C:27]3[C:20]4[C:21](=[N:22][CH:23]=[N:24][C:19]=4[N:5]4[CH2:6][CH2:7][C@@H:3]([N:2]([CH3:8])[CH3:1])[CH2:4]4)[N:25]([CH3:41])[N:26]=3)=[CH:29][N:30]=[CH:31]2)=[CH:34][CH:35]=1)[CH3:40]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 867125684-chloro-3-[1-(4-ethylphenyl)-1H-imidazol-5-yl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

生成物 1

HCID 71114548(3R)-1-{3-[1-(4-ethylphenyl)-1H-imidazol-5-yl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-N,N-dimethylpyrrolidin-3-amine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

(3R)—N,N-Dimethylpyrrolidin-3-amine (12.4 mg, 0.109 mmol) and N,N-diisopropylethylamine (14.5 mg, 0.109 mmol) were added to a solution of 4-chloro-3-[1-(4-ethylphenyl)-1H-imidazol-5-yl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (C22) (37 mg, 0.11 mmol) in acetonitrile (1 mL), and the reaction mixture was stirred at room temperature for 2 hours. After removal of volatiles in vacuo, the residue was chromatographed on silica gel (Gradient: 0% to 15% ethyl acetate in methanol) to afford the product as a glass. Yield: 13 mg, 0.031 mmol, 28%. LCMS m/z 417.1 (M+1). 1H NMR (500 MHz, CDCl3), characteristic peaks: δ 1.17 (t, J=7.6 Hz, 3H), 2.49-2.65 (m, 8H), 3.51-3.61 (br m, 1H), 3.72-3.81 (br m, 1H), 4.08 (s, 3H), 7.10 (br d, J=8.3 Hz, 2H), 7.22-7.29 (m, 2H, assumed; partially obscured by solvent peak), 7.40 (br s, 1H), 7.90 (br s, 1H), 8.29 (s, 1H).

後処理

  1. customAfter removal of volatiles in vacuo
  2. customthe residue was chromatographed on silica gel (Gradient: 0% to 15% ethyl acetate in methanol)

出典と根拠

ORDレコード
ord-06dc7a16fb854803a3165109f5b159f5
出典データセット
uspto-grants-2014_09
特許番号
US08829010B2

関連ノート

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