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Hydrochloric Acid → 1-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridin-2(1H)-one hydrochloride

HRID 882035
ノート
印刷プレビュー

反応式

HRID 882035 の反応式
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[CH:20]=[N:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=4)=[CH:13][C:12]3=[O:29])=[CH:9][CH:10]=[C:5]2[C:4]2[CH2:30][NH:31][CH2:32][CH2:33][C:3]1=2.[ClH:34]>CO.CCOCC>[ClH:34].[CH3:1][N:2]1[C:6]2=[N:7][C:8]([N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[CH:20]=[N:21][C:22]([C:25]([F:27])([F:26])[F:28])=[CH:23][CH:24]=4)=[CH:13][C:12]3=[O:29])=[CH:9][CH:10]=[C:5]2[C:4]2[CH2:30][NH:31][CH2:32][CH2:33][C:3]1=2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 575245841-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridin-2(1H)-one

生成物 1

HCID 679702261-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridin-2(1H)-one hydrochloride収率 78%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
2 回
HCID 3283Diethyl Ether溶媒

実験手順

A solution of 1-(9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridin-2(1H)-one (0.27 g, 0.59 mmol) in MeOH (2.0 mL) was treated with 1.25 M HCl in MeOH (0.47 mL, 0.59 mmol), and the resulting suspension was stirred at ambient temperature for 6 h. The suspension was diluted with Et2O, and the resulting solids were collected by filtration. The filtrate was concentrated, and the resulting residue was dissolved in CH2Cl2 (0.5 mL) and diluted with Et2O (50 mL). The resulting solids were collected by filtration. The solids from both batches were combined in Et2O and the resulting slurry was concentrated to dryness to provide the title compound (0.23 g, 78%) as an off-white powder: 280-278° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 8.89 (d, J=1.0 Hz, 1H), 8.19 (d, J=8.0, 1.5 Hz, 1H), 8.17-7.80 (m, 4H), 7.33 (d, J=8.5 Hz, 1H), 6.21 (dd, J=7.5, 2.5 Hz, 1H), 6.04 (d, J=2.5 Hz, 1H), 5.36 (s, 2H), 4.22 (s, 2H), 3.69 (s, 3H), 3.41 (t, J=6.0 Hz, 2H), 3.01 (t, J=5.5 Hz, 2H); ESI MS m/z 456 [M+H]; HPLC (Method A)>99% (AUC), tR=13.4 min.

後処理

  1. filtrationthe resulting solids were collected by filtration
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe resulting residue was dissolved in CH2Cl2 (0.5 mL)
  4. additiondiluted with Et2O (50 mL)
  5. filtrationThe resulting solids were collected by filtration
  6. concentrationthe resulting slurry was concentrated to dryness

出典と根拠

ORDレコード
ord-8e0f3b9a7ae3453db6b1e1177a87407f
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08993765B2

反応ノート

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