Triethylamine → PF-573228

HRID 1767712

反応式

HRID 1767712 の反応式
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18](=[O:23])[CH2:17][CH2:16]3)[N:3]=1.Cl.[CH3:25][S:26]([C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32][NH2:33])(=[O:28])=[O:27].C(N(CC)CC)C>CN1C(=O)CCC1>[CH3:25][S:26]([C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32][NH:33][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18](=[O:23])[CH2:17][CH2:16]3)[N:3]=1)(=[O:27])=[O:28]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 211146356-((4-Chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3,4-dihydroquinolin-2(1H)-oneHCID 447171423-(Methylsulfonyl)benzylamine hydrochloride

生成物 1

HCID 11612883PF-573228収率 54%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒2 回

反応条件

温度
100 °C

実験手順

6-(4-Chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3,4-dihydro-1H-quinolin-2-one (50 mg, 0.145 mmol) was added to 0.5 ml NMP and 3-Methanesulfonyl-benzylamine mono hydrochloride salt (32 mg, 0.145 mmoles) and triethylamine (0.060 ml, 0.435 mmoles) were added the reaction was heated to 100° C. for one hour. The reaction was cooled to room temperature and 0.5 mL NMP was added. The reaction was then filtered and purify by preparative reverse phase HPLC 30×50 mm XTerra C18 prep column, fifteen minute gradient 15-60% (0.1% NH4OH in Acetonitrile) and (0.1% NH4OH in water)), flow rate 40 mL/min. The desired product eluted (retention time 8.41 minutes) and was concentrated to a solid (38 mg, 54% yield). 1H NMR (Methanol-d4, 400 MHz) δ 2.52 (m, 2H), 2.80 (m, 2H), 2.99 (s, 3H), 4.80 (s, 2H), 6.73 (d, J=9 Hz; 1H), 7.22 (d, J=9 Hz; 1H), 7.37 (s, 1H), 7.57 (t, J=8 Hz; 1H), 7.64 (d, J=8 Hz;1H), 7.80 (m, 1H), 7.90 (s, 1H), 8.12 (s, 1H). HPLC ret. time: 5.390, LRMS (M+) 492.12.

後処理

  1. additionwere added the reaction
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationThe reaction was then filtered
  4. custompurify by preparative reverse phase HPLC 30×50 mm XTerra C18 prep column, fifteen minute gradient 15-60% (0.1% NH4OH in Acetonitrile) and (0.1% NH4OH in water)), flow rate 40 mL/min
  5. washThe desired product eluted (retention time 8.41 minutes)

出典と根拠

ORDレコード
ord-c9f8e03419d3430e9b969d03eb391c28
出典データセット
uspto-grants-2007_06
特許番号
US07235562B2

関連ノート

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