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

HRID 1398585

반응식

HRID 1398585 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-ce31449d98e14993b02b0dc668449d1c
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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