3-(2-Methoxyethyl)-2,3,4,5-tetrahydro-1h-3-benzazepin-7-amine → 5-Chloro-N(4)-[2-fluoro-6-(tetrahydro-furan-3-yloxy)-phenyl]-N(2)-[3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-pyrimidine-2,4-diamine

HRID 1687641Notes

Reaction equation

HRID 1687641 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([NH2:16])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1.Cl[C:18]1[N:23]=[C:22]([NH:24][C:25]2[C:30]([O:31][CH:32]3[CH2:36][CH2:35][O:34][CH2:33]3)=[CH:29][CH:28]=[CH:27][C:26]=2[F:37])[C:21]([Cl:38])=[CH:20][N:19]=1>>[Cl:38][C:21]1[C:22]([NH:24][C:25]2[C:30]([O:31][CH:32]3[CH2:36][CH2:35][O:34][CH2:33]3)=[CH:29][CH:28]=[CH:27][C:26]=2[F:37])=[N:23][C:18]([NH:16][C:13]2[CH:14]=[CH:15][C:8]3[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH2:11][CH2:10][C:9]=3[CH:12]=2)=[N:19][CH:20]=1

Participants

3

Reactant 2

HCID 574160893-(2-Methoxyethyl)-2,3,4,5-tetrahydro-1h-3-benzazepin-7-amineHCID 86633996(2,5-Dichloro-pyrimidin-4-yl)-[2-fluoro-6-(tetrahydro-furan-3-yloxy)-phenyl]-amine

Product 1

HCID 672646095-Chloro-N(4)-[2-fluoro-6-(tetrahydro-furan-3-yloxy)-phenyl]-N(2)-[3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-pyrimidine-2,4-diamine

Procedure

Title compound was prepared from 3-(2-Methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine and (2,5-Dichloro-pyrimidin-4-yl)-[2-fluoro-6-(tetrahydro-furan-3-yloxy)-phenyl]-amine in an analogous manner to Example 1221d. Title compound was isolated as a white solid (60 mg, 42%). HPLC purity 99%, LCMS=528.17 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 11.79 (s, 1H), 7.92 (s, 1H), 7.42-7.38 (m, 2H), 7.24-7.19 (m, 2H), 6.95-6.91 (m, 2H), 6.77 (d, J=8.4 Hz, 1H), 4.92 (s, 1H), 3.87-3.80 (m, 8H), 3.45-3.40 (m, 7H), 2.90-2.80 (m, 3H), 2.65-2.55 (m, 1H), 2.30-2.24 (m, 1H), 2.22-2.10 m, 1H).

Sources & evidence

ORD record
ord-21c4fae3e76344c99be42b9ed7011862
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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