Acetyl chloride → 6-[Acetyl(ethyl)amino]-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide

HRID 1037534ノート

反応式

HRID 1037534 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:19][CH3:20])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([NH:24][CH2:25][CH3:26])[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:36](Cl)(=[O:38])[CH3:37]>C(Cl)Cl>[C:36]([N:24]([CH2:25][CH3:26])[C:12]1[C:13]([CH:21]2[CH2:23][CH2:22]2)=[CH:14][C:15]2[C:10]([CH:11]=1)=[N:9][N:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:16]=2[C:17]([NH:19][CH3:20])=[O:18])(=[O:38])[CH3:37]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 675178472-(4-bromophenyl)-5-cyclopropyl-6-(ethylamino)-N-methyl-2H-indazole-3-carboxamide

生成物 1

HCID 569631716-[Acetyl(ethyl)amino]-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide収率 61%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of compound (ii) (6 mg, 0.015 mmol) in DCM was added DIPEA (7 μL, 0.040 mmol), followed by acetyl chloride (7 μL, 0.098 mmol) and the reaction was stirred at RT for 20 min. After concentrating to dryness, the residue was purified by flash column chromatography eluting with MeOH/DCM (0-20%) to give Compound (48) as a white solid (4 mg, 61%). ESI-MS m/z calculated for [M+H]+: 455.1/457.1; found: 455.4/457.4; 1H NMR (400 MHz, CDCl3) δ 7.71-7.63 (m, 2H), 7.56 (brs, 1H), 7.52-7.46 (m, 2H), 7.43 (s, 1H), 5.77 (brs, 1H), 4.32 (dq, J=14.3, 7.2 Hz, 1H), 3.25 (dq, J=14.2, 7.1 Hz, 1H), 3.01 (d, J=4.9 Hz, 3H), 1.96-1.74 (m, 4H), 1.21 (t, J=7.2 Hz, 3H), 1.10-0.97 (m, 2H), 0.86-0.70 (m, 2H).

後処理

  1. concentrationAfter concentrating to dryness
  2. customthe residue was purified by flash column chromatography
  3. washeluting with MeOH/DCM (0-20%)

出典と根拠

ORDレコード
ord-71f325e631c1430fa4859b0ee651d12a
出典データセット
uspto-grants-2013_10
特許番号
US08546389B2

反応ノート

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