7-[4-(4-Methyl-piperazin-1-yl)-piperidin-1-yl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine → [2-(5-Chloro-2-{7-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamino]-pyrimidin-4-ylamino)-3-fluoro-phenoxy]-acetonitrile

HRID 1041494Notes

Reaction equation

HRID 1041494 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:10]=2[O:11][CH2:12][C:13]#[N:14])[C:5]([Cl:20])=[CH:4][N:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH:28]2[CH2:33][CH2:32][N:31]([CH:34]3[CH2:40][CH2:39][C:38]4[CH:41]=[C:42]([NH2:45])[CH:43]=[CH:44][C:37]=4[CH2:36][CH2:35]3)[CH2:30][CH2:29]2)[CH2:24][CH2:23]1>>[Cl:20][C:5]1[C:6]([NH:8][C:9]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:10]=2[O:11][CH2:12][C:13]#[N:14])=[N:7][C:2]([NH:45][C:42]2[CH:43]=[CH:44][C:37]3[CH2:36][CH2:35][CH:34]([N:31]4[CH2:32][CH2:33][CH:28]([N:25]5[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]5)[CH2:29][CH2:30]4)[CH2:40][CH2:39][C:38]=3[CH:41]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 672641617-[4-(4-Methyl-piperazin-1-yl)-piperidin-1-yl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamineHCID 86633948[2-(2,5-Dichloropyrimidin-4-ylamino)-3-fluorophenoxy]-acetonitrile

Product 1

HCID 67263785[2-(5-Chloro-2-{7-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamino]-pyrimidin-4-ylamino)-3-fluoro-phenoxy]-acetonitrile

Procedure

The title compound was prepared by combining [2-(2,5-dichloro-pyrimidin-4-ylamino)-3-fluoro-phenoxy]-acetonitrile (Example N?, 31.3 mg, 0.100 mmol) and 7-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine (Example N?, 25.2 mg, 0.074 mmol) in an analogous manner described in Example 151d. The title product was isolated as described in Example 1475b as a white foam (33 mg, 66%) that had the following properties: m.p: 110-116° C.; LC/MS (m/e): 620 (M+H); 1H-NMR (CDCl3, 400 MHz): δ 8.10 (s, 1H), 7.36 (dd, J=14.7, 7.81H), 7.14 (s, 1H), 7.05 (d, J=6.9, 1H), 7.01 (d, J=8.7, 1H), 6.94-6.90 (m, 2H), 6.88 (s, 1H), 6.50 (s, 1H), 4.73 (s, 2H), 2.90-2.80 (m, 2H), 2.75-2.35 (m, 10H), 2.30 (s, 3H), 2.30-2.18 (m, 2H), 2.10-2.00 (m, 2H), 1.85-1.65 (m, 4H), 1.65-1.45 (m, 2H) 1.40-1.20 (m, 4H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-33a4d3d56b774fb7a2898665432a4baa
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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