4-(3-(Pyrrolidin-1-yl)propyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine → HCID 178511899、化合物

HRID 1917198ノート

反応式

HRID 1917198 の反応式
[N:1]1([CH2:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][S:12][C:11]3[CH:15]=[C:16]([NH2:19])[CH:17]=[CH:18][C:10]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.I.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](SC)=[NH:27]>C(O)C.C([O-])(O)=O.[Na+]>[N:1]1([CH2:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][S:12][C:11]3[CH:15]=[C:16]([NH:19][C:26]([C:22]4[S:21][CH:25]=[CH:24][CH:23]=4)=[NH:27])[CH:17]=[CH:18][C:10]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 591440974-(3-(Pyrrolidin-1-yl)propyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

生成物 1

HCID 178511899HCID 178511899、化合物収率 85.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A solution of 4-(3-(pyrrolidin-1-yl)propyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine (0.43 g, 1.550 mmol) in dry ethanol (15 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.884 g, 3.10 mmol) at room temperature, and the resulting mixture was stirred overnight (18 hours). The reaction was diluted with saturated NaHCO3 solution (30 mL), and the product was extracted into CH2Cl2 (3×20 mL). The combined CH2Cl2 layers were washed with brine (20 mL) and then dried (Na2SO4). The solvent was evaporated, and the crude material was purified by column chromatography (5:95 (2 M NH3 in MeOH):CH2Cl2), to obtain the title product 21 (0.51 g, 85%) as a solid. 1H NMR (DMSO-d6) δ 7.68 (d, 1H, J=4.5 Hz), 7.55 (d, 1H, J=5.1 Hz), 7.06 (dd, 1H, J=3.6, 4.9 Hz), 6.70 (d, 1H, J=8.7 Hz), 6.52-6.44 (m, 2H), 6.32 (brs, 2H), 3.51-3.48 (m, 2H), 3.27 (t, 2H, J=7.2 Hz), 3.04-3.00 (m, 2H), 2.48-2.40 (m, 6H), 1.80-1.60 (m, 6H); ESI-MS (m/z, %): 387 (MH+, 68), 276 (100), 194 (75); HPLC purity: 98.32% by area.

後処理

  1. extractionthe product was extracted into CH2Cl2 (3×20 mL)
  2. washThe combined CH2Cl2 layers were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated
  5. customthe crude material was purified by column chromatography (5:95 (2 M NH3 in MeOH):CH2Cl2)

出典と根拠

ORDレコード
ord-d0fec40cf9134a52b3e7ed76bdc9aaf4
出典データセット
uspto-grants-2013_12
特許番号
US08618286B2

反応ノート

読み込み中…