2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)ethan-1-ol → 7-{5-Chloro-2-[3-(2-hydroxy-ethyl)-8-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamino]-pyrimidin-4-ylamino}-4-(4-isopropyl-piperazin-1-yl)-2-methyl-2,3-dihydro-isoindol-1-one

HRID 1687515Notes

Reaction equation

HRID 1687515 reaction equation
[NH2:1][C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][OH:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.Cl[C:19]1[N:24]=[C:23]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([N:37]3[CH2:42][CH2:41][N:40]([CH:43]([CH3:45])[CH3:44])[CH2:39][CH2:38]3)=[C:30]3[C:34]=2[C:33](=[O:35])[N:32]([CH3:36])[CH2:31]3)[C:22]([Cl:46])=[CH:21][N:20]=1>>[Cl:46][C:22]1[C:23]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([N:37]3[CH2:38][CH2:39][N:40]([CH:43]([CH3:45])[CH3:44])[CH2:41][CH2:42]3)=[C:30]3[C:34]=2[C:33](=[O:35])[N:32]([CH3:36])[CH2:31]3)=[N:24][C:19]([NH:1][C:2]2[C:15]([O:16][CH3:17])=[CH:14][C:5]3[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][OH:13])[CH2:9][CH2:10][C:4]=3[CH:3]=2)=[N:20][CH:21]=1

Participants

3

Reactant 2

HCID 574161162-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)ethan-1-olHCID 598492227-(2,5-Dichloropyrimidin-4-ylamino)-4-(4-isopropylpiperazin-1-yl)-2-methyl-2,3-dihydroisoindol-1-one

Product 1

HCID 668300637-{5-Chloro-2-[3-(2-hydroxy-ethyl)-8-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamino]-pyrimidin-4-ylamino}-4-(4-isopropyl-piperazin-1-yl)-2-methyl-2,3-dihydro-isoindol-1-one

Procedure

The title compound was prepared from 2-(7-amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-ethanol (40 mg, 0.20 mmol) and 7-(2,5-dichloropyrimidin-4-ylamino)-4-(4-isopropylpiperazin-1-yl)-2-methyl-2,3-dihydroisoindol-1-one (74 mg, 0.17 mmol) in an analogous manner to Example 946 to afford an off-white solid (75 mg, 70%). Mp: 198-200° C. LCMS (m/e) 635 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 10.55 (s, 1H), 8.67 (d, J=9 Hz, 1H), 8.11 (s, 2H), 7.40 (s, 1H), 7.10 (d, J=9 Hz, 1H), 6.68 (s, 1H), 4.40 (s, 2H), 3.91 (s, 3H), 3.70 (m, 2H), 3.20 (s, 3H), 3.08 (m, 4H), 2.92 (m, 5H), 2.82-2.64 (m, 11H), 1.13 (d, J=6 Hz, 6H).

Sources & evidence

ORD record
ord-5b8bdefbe7c34d61988b862959fe1fba
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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