4-[4-(4-acetylpiperazin-1-yl)cyclohexyl]-7-amino-2-methyl-2,3-dihydro-1H-isoindol-1-one → HCID 178476861, compound

HRID 1948054Notes

Reaction equation

HRID 1948054 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21](Cl)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=2)=[C:12]([O:28][CH3:29])[CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[C:30]([N:33]1[CH2:38][CH2:37][N:36]([CH:39]2[CH2:44][CH2:43][CH:42]([C:45]3[CH:53]=[CH:52][C:51]([NH2:54])=[C:50]4[C:46]=3[CH2:47][N:48]([CH3:56])[C:49]4=[O:55])[CH2:41][CH2:40]2)[CH2:35][CH2:34]1)(=[O:32])[CH3:31]>>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21]([NH:54][C:51]3[CH:52]=[CH:53][C:45]([C@H:42]4[CH2:43][CH2:44][C@H:39]([N:36]5[CH2:35][CH2:34][N:33]([C:30](=[O:32])[CH3:31])[CH2:38][CH2:37]5)[CH2:40][CH2:41]4)=[C:46]4[C:50]=3[C:49](=[O:55])[N:48]([CH3:56])[CH2:47]4)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=2)=[C:12]([O:28][CH3:29])[CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

3

Reactant 2

HCID 672564554-[4-(4-acetylpiperazin-1-yl)cyclohexyl]-7-amino-2-methyl-2,3-dihydro-1H-isoindol-1-one2×HCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Product 1

HCID 178476861HCID 178476861, compound

Procedure

The title compounds were prepared according to the procedure for Example 102 using diethyl(4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate and 4-[4-(4-acetyl piperazin-1-yl)cyclohexyl]-7-amino-2-methyl-2,3-dihydro-1H-isoindol-1-one (Compound 237A). The reaction mixture was purified by MDP. Example 237 was first peak to elute. 1H NMR (CDCl3, 400 MHz): δ=1.28 (t, J=6.95 Hz, 6H), 1.50-1.73 (m, 7H), 2.02 (s, 2H), 2.12 (s, 3H), 2.50 (br. s., 2H), 2.62 (br. s., 3H), 3.13-3.21 (m, 2H), 3.22 (s, 3H), 3.42-3.75 (m, 4H), 3.93 (s, 3H), 3.99-4.10 (m, 4H), 4.38 (s, 2H), 6.90 (dt, J=8.08, 2.15 Hz, 1H), 6.94 (t, J=2.02 Hz, 1H), 7.34 (d, J=8.84 Hz, 1H), 7.63 (s, 1H), 8.28 (d, J=7.58 Hz, 1H), 8.40 (s, 1H), 8.64 (d, J=8.59 Hz, 1H), 10.51 (s, 1H). MS (ES+): m/z 788.31 [MH+] (TOF, polar). Example 238 eluted afterwards: 1H NMR (CDCl3, 400 MHz): δ=1.28 (t, J=7.07 Hz, 6H), 1.87 (d, J=4.04 Hz, 2H), 1.91-2.03 (m, 2H), 2.12-2.25 (m, 7H), 2.84 (br. s., 2H), 3.21 (s, 3H), 3.23-3.33 (m, 4H), 3.86 (s, 3H), 3.93 (br. s., 2H), 4.04 (qdd, J=7.31, 7.31, 7.31, 7.14, 1.77 Hz, 4H), 4.38 (s, 2H), 6.94-7.00 (m, 2H), 7.36 (d, J=7.83 Hz, 1H), 7.71 (br. s., 1H), 8.23 (br. s., 2H), 11.20 (br. s., 1H). MS (ES+): m/z 788.31 [MH+] (TOF, polar).

Workup

  1. customThe reaction mixture was purified by MDP
  2. washto elute
  3. washExample 238 eluted afterwards

Sources & evidence

ORD record
ord-2147dce0d430447b9ba16195393bea78
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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