2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)ethan-1-ol → HCID 67263780, compound

HRID 1687865Notes

Reaction equation

HRID 1687865 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[C@@H:14]3[CH2:15][C@@H:11]([CH:12]=[CH:13]3)[C@@H:10]2[C:16]([NH2:18])=[O:17])[C:5]([Cl:19])=[CH:4][N:3]=1.[NH2:20][C:21]1[C:34]([O:35][CH3:36])=[CH:33][C:24]2[CH2:25][CH2:26][N:27]([CH2:30][CH2:31][OH:32])[CH2:28][CH2:29][C:23]=2[CH:22]=1>>[Cl:19][C:5]1[C:6]([NH:8][C@@H:9]2[C@@H:14]3[CH2:15][C@@H:11]([CH:12]=[CH:13]3)[C@@H:10]2[C:16]([NH2:18])=[O:17])=[N:7][C:2]([NH:20][C:21]2[C:34]([O:35][CH3:36])=[CH:33][C:24]3[CH2:25][CH2:26][N:27]([CH2:30][CH2:31][OH:32])[CH2:28][CH2:29][C:23]=3[CH:22]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 574161162-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)ethan-1-olHCID 57522618HCID 57522618, compound

Product 1

HCID 67263780HCID 67263780, compoundYield 42%

Procedure

In an analogous manner to Example 1503, the product was prepared from (1S,2S,3R,4R)-3-(2,5-Dichloro-pyrimidin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide and 2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-ethanol. Product was isolated as a white foam (35 mg, 42%). MS (ESI+): 499 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 8.22 (s, 1H), 7.91 (s, 1H), 7.42 (s, 1H), 6.66 (s, 1H), 6.57 (s, 1H), 6.51 (s, 1H), 6.33 (s, 2H), 5.60 (s, 1H), 5.35 (s, 1H), 5.32 (s, 1H), 4.47 (t, J=8 Hz, 1H), 3.89 (s, 3H), 3.84 (s, 2H), 3.63 (d, 5H), 3.09 (s, 1H), 2.89-2.69 (m, 20H), 2.53 (d, J=9 Hz, 1H), 2.28 (d, J=9 Hz, 1H), 1.67 (d, J=9 Hz, 1H).

Sources & evidence

ORD record
ord-41ce99bc43b04ae4b85c664f485e5512
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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