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Diisopropylethylamine → (+/-)-N4-(3,4-difluorophenyl)-5-fluoro-N2-[2,3-dihydro-2-(N-methylamino)carbonylbenzofuran-5-yl]-2,4-pyrimidinediamine

HRID 578520
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인쇄 미리보기

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HRID 578520 반응식
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]([F:16])=[CH:14][N:13]=[C:12]([NH:17][C:18]3[CH:19]=[CH:20][C:21]4[O:25][CH:24]([C:26]([O:28]C)=O)[CH2:23][C:22]=4[CH:30]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl.CN.[CH:34]([N:37](C(C)C)CC)(C)C>CO.O>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]([F:16])=[CH:14][N:13]=[C:12]([NH:17][C:18]3[CH:19]=[CH:20][C:21]4[O:25][CH:24]([C:26]([NH:37][CH3:34])=[O:28])[CH2:23][C:22]=4[CH:30]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]
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참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 22060930(+)-N4-(3,4-difluorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine

생성물 1

HCID 22060649(+/-)-N4-(3,4-difluorophenyl)-5-fluoro-N2-[2,3-dihydro-2-(N-methylamino)carbonylbenzofuran-5-yl]-2,4-pyrimidinediamine

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 962Water용매

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온도
80 °C

실험 절차

A mixture of (±)-N4-(3,4-difluorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine, methylamine Hydrogen Chloride (5 equivalents) and diisopropylethylamine (5 equivalents) in MeOH was shaken in a sealed tube at 80° C. for 24 h. The resulting solution was diluted with water and the precipitate obtained was filtered, washed with water, dried and analyzed to afford (±)-N4-(3,4-difluorophenyl)-5-fluoro-N2-[2,3-dihydro-2-(N-methylamino)carbonylbenzofuran-5-yl]-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.46 (s, 1H), 9.07 (s, 1H), 8.05 (m, 3H), 7.48 (m, 2H), 7.35 (m, 1H), 7.22 (m, 1H), 6.72 (d, 1H, J=8.1 Hz), 5.07 (dd, 1H, J=6.6 and 6.3 Hz), 3.40 (dd, 1H), 3.15 (dd, 1H), 2.60 (d, 3H, J=4.5 Hz); LCMS: purity: 98%; MS (m/e): 416 (MH+).

후처리

  1. customthe precipitate obtained
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried

출처 및 근거

ORD 기록
ord-f690dac225e54c24b96f2674a8c0125f
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040550B2

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