2H-1-Benzazepin-2-one, 8-amino-1-ethyl-1,3,4,5-tetrahydro- → HCID 66830515, compound

HRID 1041265Notes

Reaction equation

HRID 1041265 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2OCC#N)[C:5]([Cl:19])=[CH:4][N:3]=1.[NH2:20][C:21]1[CH:34]=[CH:33][C:24]2[CH2:25][CH2:26][CH2:27][C:28](=[O:32])[N:29]([CH2:30][CH3:31])[C:23]=2[CH:22]=1>>[Cl:19][C:5]1[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[CH2:6][CH2:5][C:4]#[N:3])=[N:7][C:2]([NH:20][C:21]2[CH:34]=[CH:33][C:24]3[CH2:25][CH2:26][CH2:27][C:28](=[O:32])[N:29]([CH2:30][CH3:31])[C:23]=3[CH:22]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 98991662H-1-Benzazepin-2-one, 8-amino-1-ethyl-1,3,4,5-tetrahydro-HCID 86633910[2-(2,5-Dichloropyrimidin-4-ylamino)-phenoxy]acetonitrile

Product 1

HCID 66830515HCID 66830515, compound

Procedure

3-{2-[5-Chloro-2-(1-ethyl-2-oxo-2,3,4,5-tetrahydr o-1H-1-benzazepin-8-ylamino)-pyrimidin-4-ylamino]-phenyl}-propionitrile was prepared from [2-(2,5-Dichloro-pyrimidin-4-ylamino)-phenoxy]-acetonitrile and 8-Amino-1-ethyl-1,3,4,5-tetrahydro-1-benzazepin-2-one (from Example 358a) in an analogous manner to Example 1221d. (120° C., 40 min) Obtained 83 mg (76%) as a white foam. HPLC purity: 90%, LCMS 461.22 (M+H), 1H-NMR (CDCl3, 400 MHz) δ: 8.09 (s, 1H), 7.46-7.42 (m, 1H), 7.41-7.31 (m, 4H), 7.28 (s, 1H), 7.05-6.92 (m, 3H), 4.00-3.20 (bm, 2H), 2.97 (t, J=7.2 Hz, 2 h), 2.61 (t, J=7.2 Hz, 2H), 2.28-2.22 (m, 2H), 2.22-2.2.05 (m, 2H), 1.00 (t, J=7.1 Hz, 3H).

Workup

  1. custom(120° C., 40 min) Obtained 83 mg (76%) as a white foam

Sources & evidence

ORD record
ord-de583029a4bd4a088069598443d1d8ad
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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