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Hydrochloric Acid → 1-(6-Methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-one hydrochloride

HRID 474911
ノート
印刷プレビュー

反応式

HRID 474911 の反応式
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=4)=[CH:13][C:12]3=[O:27])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:28][N:29](C(OC(C)(C)C)=O)[CH2:30][CH2:31][CH2:32][C:3]1=2.[ClH:40]>CO>[ClH:40].[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:18]=[N:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=4)=[CH:13][C:12]3=[O:27])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:28][NH:29][CH2:30][CH2:31][CH2:32][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

4

反応物 2

HCID 313Hydrochloric AcidHCID 66873773tert-Butyl 6-methyl-8-(2-oxo-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-1(2H)-yl)3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate

生成物 1

HCID 668731281-(6-Methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-one hydrochloride収率 70%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of tert-butyl 6-methyl-8-(2-oxo-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-1(2H)-yl)3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (67 mg, 0.13 mmol) in 1.25 M HCl in MeOH (16 mL) was stirred at ambient temperature for 18 h. The mixture was concentrated to dryness under reduced pressure and diluted with MeOH (2.0 mL) and Et2O (25 mL). The resulting solids were collected by filtration and dried to yield the title compound (42 mg, 70%) as a yellow powder: mp 274-280° C. decomp; 1H NMR (500 MHz, DMSO-d6) δ 9.50 (s, 2H), 9.20 (d, J=2.0 Hz, 1H), 8.50 (dd, J=8.0, 2.0 Hz, 1H), 8.05 (d, J=8.0 Hz, 1H), 7.86 (d, J=7.0 Hz, 1H), 7.69 (d, J=8.5 Hz, 1H), 7.59 (d, J=1.5 Hz, 1H), 7.09 (dd, J=8.5, 2.0 Hz, 1H), 7.00 (d, J=2.0 Hz, 1H), 6.80 (d, J=7.5, 2.0 Hz, 1H), 4.42-4.41 (m, 2H), 3.73 (s, 3H), 3.43-3.41 (m, 2H), 3.11 (t, J=6.0 Hz, 2H), 2.10-2.08 (m, 2H); ESI MS m/z 439 [M+H]+; HPLC (Method A) 99.0% (AUC), tR=13.7 min.

後処理

  1. concentrationThe mixture was concentrated to dryness under reduced pressure
  2. additiondiluted with MeOH (2.0 mL) and Et2O (25 mL)
  3. filtrationThe resulting solids were collected by filtration
  4. customdried

出典と根拠

ORDレコード
ord-611a1b54cb514b63bc3749e62e5b2578
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08637501B2

反応ノート

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