Triethylamine → 1-(2-aminopyrimidin-4-yl)-6-iodo-N-methyl-N-(pyridin-2-yl)indazole-3-carboxamide

HRID 1398585

反応式

HRID 1398585 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([I:17])[CH:15]=3)[C:10]([C:18](Cl)=[O:19])=[N:9]2)[CH:5]=[CH:4][N:3]=1.[CH3:21][NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(CC)CC)C>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([I:17])[CH:15]=3)[C:10]([C:18]([N:22]([CH3:21])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[O:19])=[N:9]2)[CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 207272-Pyridinamine, N-methyl-HCID 866695951-(2-Aminopyrimidin-4-yl)-6-iodoindazole-3-carbonyl chloride

生成物 1

HCID 681818351-(2-aminopyrimidin-4-yl)-6-iodo-N-methyl-N-(pyridin-2-yl)indazole-3-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-(2-aminopyrimidin-4-yl)-6-iodoindazole-3-carbonyl chloride (330 mg, 0.83 mmol) in DCM (5 mL) was added N-methylpyridin-2-amine (0.1 ml, 0.99 mmol) followed by triethylamine (0.29 ml, 2.06 mmol). The reaction was stirred at RT overnight and then concentrated in vacuo. The residue was diluted with water (10 ml) and extracted with DCM (2×20 ml). The title intermediate was obtained as a precipitate which was collected by suction filtration. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The precipitate and organic extracts were combined to give the crude title intermediate; LC-MS purity=79%: 1H NMR (500 MHz, DMSO) delta 3.54 (3H, s), 6.28 (1H, d, J=5.5 Hz), 7.15 (2H, s), 7.25 (1H, dd, J=6.7, 5.0 Hz), 7.40 (1H, d, J=8.1 Hz), 7.74 (1H, dd, J=8.5, 1.3 Hz), 7.79-7.84 (2H, m), 8.19 (1H, d, J=5.5 Hz), 8.32 (1H, dd, J=4.6, 1.5 Hz), 9.24 (1H, s); LC-MS: m/z=+472.00 (M+H)+.

後処理

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with water (10 ml)
  3. extractionextracted with DCM (2×20 ml)

出典と根拠

ORDレコード
ord-ce31449d98e14993b02b0dc668449d1c
出典データセット
uspto-grants-2014_12
特許番号
US08901313B2

関連ノート

読み込み中…