Triethylamine → 2-(4-Chloro-phenyl)-2-hydroxy-n-[3-(2-methyl-2h-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-acetamide

HRID 1362946

反応式

HRID 1362946 の反応式
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH2:21])[CH:10]=[CH:11][C:12]=2[O:13][CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=[N:3]1.[Cl:22][C:23]1[CH:33]=[CH:32][C:26]([CH:27]([OH:31])[C:28](O)=[O:29])=[CH:25][CH:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([CH:27]([OH:31])[C:28]([NH:21][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[C:7]([C:6]3[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=3)[CH:8]=2)=[O:29])=[CH:32][CH:33]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 102994-Chloromandelic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 468324843-(1-methyl-1H-pyrazol-5-yl)-4-(2-(pyrrolidin-1-yl)ethoxy)benzenamine

生成物 1

HCID 589643172-(4-Chloro-phenyl)-2-hydroxy-n-[3-(2-methyl-2h-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-acetamide収率 15.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 3-(2-methyl-2H-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (100 mg, 0.35 mmol), 4-chloromandelic acid (98 mg, 0.525 mmol), HATU (200 mg, 0.525 mmol) and triethylamine (0.5 mL) in DMF (6 mL) was heated at 50° C. overnight. The crude was purified by HPLC to provide the title compound as a semi-solid (24 mg, i 5%). 1H NMR (DMSO-d6, 400 MHz) δ 1.60-1.73 (m, 2H), 1.84-1.91 (m, 2H), 2.80-2.90 (m, 2H), 3.22-3.30 (m, 4H), 3.65 (s, 3H), 4.25 (t, J=5.05 Hz, 2H), 6.26 (d, J=1.77 Hz, 1H), 7.17 (d, J=9.09 Hz, 1H), 7.39-7.46 (m, 2H), 7.51-7.53 (m 3H), 7.67 (d, J=2.53 Hz, 1H), 7.80 (dd, J=2.78, 8.84 Hz, 1H), 9.50 (s br, 1H), 10.0 (s, 1H). Exact mass calculated for C24H27ClN4O3 454.2. found 455.4 (M+).

後処理

  1. customThe crude was purified by HPLC

出典と根拠

ORDレコード
ord-7d422b9c75b0478ba2b2070e2b7df4ea
出典データセット
uspto-grants-2011_02
特許番号
US07884101B2

関連ノート

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