Bis(2-oxo-3-oxazolidinyl)phosphinic chloride → HCID 178489391、化合物

HRID 2388962

反応式

HRID 2388962 の反応式
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[CH:13]=[C:14]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])=[N:19][NH:18][C:15]3=[N:16][CH:17]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[CH3:44][N:45]([CH3:54])[CH2:46][CH2:47][N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1>CC(N(C)C)=O>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[CH:13]=[C:14]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])=[N:19][NH:18][C:15]3=[N:16][CH:17]=2)=[CH:7][C:3]=1[C:4]([N:51]1[CH2:52][CH2:53][N:48]([CH2:47][CH2:46][N:45]([CH3:54])[CH3:44])[CH2:49][CH2:50]1)=[O:6]

参加物

5

反応物 3

HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 27362291-(2-(Dimethylamino)ethyl)piperazineHCID 178489392HCID 178489392、化合物

生成物 1

HCID 178489391HCID 178489391、化合物収率 31%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

45 mg (0.12 mmol) of 2-amino-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-3-methyl-benzoic acid and 40 mg (0.16 mmol) of bis(2-oxo-3-oxazolidinyl)-phosphinic chloride were dissolved in 2 mL of dimethyl acetamide. 45 μL (approx. 0.2 mmol; density unknown) of 1-(2-dimethylaminoethyl)-piperazine was added and the mixture irradiated in a Personal Chemistry® Optimizer to 120° C. for 30 min. The resulting crude was directly purified by mass-triggered reverse-phase HPLC to afford 19 mg (37 μmol, 31%) of {2-amino-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-3-methyl-phenyl}-[4-(2-dimethylamino-ethyl)-piperazin-1-yl]-methanone as an ivory solid. 1H NMR (500 MHz, DMSO-d6) δ 13.71 (s, br., 1H), 8.75 (d, 1H), 8.16 (d, 1H), 7.63 (dd, 1H), 7.46 (dd(d), 1H), 7.44 (m, 1H), 7.22 (m, 1H), 7.21 (m, 1H), 7.09 (dd(d, 1H), 5.01 (s, 2H), 3.84 (s, 3H), 3.48 (m, br., 4H), 2.45-2.30 (m, 6H), 2.19 (s, 3H), 2.13 (s, 6H), MS: m/z 514.2 (M+H+).

後処理

  1. customthe mixture irradiated in a Personal Chemistry® Optimizer to 120° C. for 30 min
  2. customThe resulting crude was directly purified by mass-triggered reverse-phase HPLC

出典と根拠

ORDレコード
ord-a7e61661db424cbb87216cced10fdf7a
出典データセット
uspto-grants-2012_09
特許番号
US08268994B2

関連ノート

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