Methylamine → US10633389, Example 3-1

HRID 527467노트

반응식

HRID 527467 반응식
[CH3:1][C:2]1[C:3]([NH:25][C@@H:26]2[CH2:30][CH2:29][O:28][CH2:27]2)=[N:4][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH:22]3[CH2:24][O:23]3)[CH:15]=2)=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[CH3:31][NH2:32]>CO>[CH3:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][C:5]([C:14]2[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=2)[O:20][CH2:21][CH:22]([OH:23])[CH2:24][NH:32][CH3:31])=[N:4][C:3]=1[NH:25][C@@H:26]1[CH2:30][CH2:29][O:28][CH2:27]1

참가 물질

4

반응물 2

HCID 6329MethylamineHCID 904256505-Methyl-6-morpholino-2-(3-(oxiran-2-ylmethoxy)phenyl)-N-((R)-tetra-hydrofuran-3-yl)pyrimidin-4-amine

생성물 1

HCID 90426219US10633389, Example 3-1수율 37%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

5-Methyl-6-morpholino-2-(3-(oxiran-2-ylmethoxy)phenyl)-N—((R)-tetra-hydrofuran-3-yl)pyrimidin-4-amine (20 mg, 0.05 mmol) was dissolved in a 2N MeNH2 solution in methanol, (10 mL) and the mixture was stirred at room temperature for 14 h., concentrated under vacuum and the residue was purified by preparative HPLC to obtain the 1-(3-(5-methyl-4-morpholino-6-((R)-tetrahydrofuran-3-ylamino)pyrimidin-2-yl)phenoxy)-3-(methyl-amino)propan-2-ol (8 mg, 37% yield) as a white solid. 1H NMR (500 MHz, CD3OD) δ ppm: 8.02-7.96 (m, 2H), 7.34 (t, J=8.0 Hz, 1H), 7.05-7.00 (m, 1H), 4.85-4.80 (m, 1H), 4.20-4.14 (m, 2H), 4.07-4.01 (m, 3H), 3.93-3.84 (m, 5H), 3.78-3.74 (m, 1H), 2.96-2.92 (m, 1H), 2.88-2.82 (m, 1H), 2.53 (s, 3H), 2.42-2.35 (m, 1H), 2.11-2.04 (m, 4H); ESI-LCMS (m/z): 444.3 [M+1]+.

후처리

  1. concentrationconcentrated under vacuum
  2. customthe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-799adaf154374a338becc40df315a6fa
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346802B2

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