Benzylamine → 5-[1-(2,3-Difluorobenzyl)piperidin-4-ylmethoxy]quinazoline-2,4-diamine

HRID 1015337

반응식

HRID 1015337 반응식
C(N)C1C=CC=CC=1.[NH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][O:16][C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[C:19]([NH2:28])=[N:20][C:21]([NH2:27])=[N:22]3)[CH2:11][CH2:10]1.[F:29][C:30]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32]Br>>[F:29][C:30]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][O:16][C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[C:19]([NH2:28])=[N:20][C:21]([NH2:27])=[N:22]3)[CH2:11][CH2:10]1

참가 물질

4

반응물 3

HCID 7504BenzylamineHCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

생성물 1

HCID 250077865-[1-(2,3-Difluorobenzyl)piperidin-4-ylmethoxy]quinazoline-2,4-diamine수율 53%

실험 절차

The benzylamine was obtained by reacting 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (50 mg; 0.18 mmol) and 2,3-difluorobenzyl bromide (77 mg; 0.37 mmol) via Method BB to yield 38 mg. (53% yield). 1HNMR (400 MHz, DMSO-d6) δ 8.26 (br s, 1H), 7.8 (br s, 1H), 7.55 (t, J=8.4 Hz, 1H), 7.33 (m, 1H), 7.2 (m, 2H), 6.99 (br s, 2H), 6.9 (d, J=8 Hz, 1H), 6.81 (d, J=8.0 Hz, 2H), 4.07 (d, J=6.4 Hz, 2H), 3.59 (s, 2H), 2.85 (m, 2H), 2.04 (t, J=11.2 Hz, 2H), 1.9 (m, 1H), 1.73 (d, J=10.4 Hz, 2H), 1.33 (m, 2H). MS m/z (ESI) 400 (M+H)+.

후처리

  1. customto yield 38 mg

출처 및 근거

ORD 기록
ord-6cadd087a84c45209c4d7351ee0b5d24
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985755B2

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