7-amino-4-(4-hydroxycyclohexyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one → HCID 178496530, compound

HRID 1947993Notes

Reaction equation

HRID 1947993 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][P:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[N:26]=[C:25](Cl)[C:24]([C:28]([F:31])([F:30])[F:29])=[CH:23][N:22]=2)=[CH:16][CH:15]=1)(=[O:12])[O:7][CH2:8][CH2:9][O:10][CH3:11].[NH2:32][C:33]1[CH:34]=[CH:35][C:36]([CH:44]2[CH2:49][CH2:48][CH:47]([OH:50])[CH2:46][CH2:45]2)=[C:37]2[C:41]=1[C:40](=[O:42])[N:39]([CH3:43])[CH2:38]2>>[CH3:1][O:2][CH2:3][CH2:4][O:5][P:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[N:26]=[C:25]([NH:32][C:33]3[CH:34]=[CH:35][C:36]([C@H:44]4[CH2:45][CH2:46][C@H:47]([OH:50])[CH2:48][CH2:49]4)=[C:37]4[C:41]=3[C:40](=[O:42])[N:39]([CH3:43])[CH2:38]4)[C:24]([C:28]([F:31])([F:30])[F:29])=[CH:23][N:22]=2)=[CH:16][CH:15]=1)(=[O:12])[O:7][CH2:8][CH2:9][O:10][CH3:11]

Participants

3

Reactant 2

HCID 672549257-amino-4-(4-hydroxycyclohexyl)-2-methyl-2,3-dihydro-1H-isoindol-1-oneHCID 86654036Bis(2-methoxyethyl)(4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate2×

Product 1

HCID 178496530HCID 178496530, compound

Procedure

The title product was prepared according to the procedure for Example 102 using bis(2-methoxyethyl)(4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate (Compound 189A, 39.5 mg, 0.0816 mmol) and 7-amino-4-(4-hydroxycyclohexyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one (24.7 mg, 0.0949 mmol). The reaction mixture concentrated and purified by MDP [under basic conditions; ammonium bicarbonate basic buffer (pH 9)]. The title compound was obtained as a white solid, 36.2 mg (61%). 1H NMR (400 MHz, DMSO-d6) δ 10.58 (br s, 1H), 9.89 (s, 1H), 8.46 (s, 1H), 8.65 (br s, 1H), 7.57 (br s, 2H), 7.38 (d, J=8.8 Hz, 1H), 7.26 (dd, J=8.6, 2.0 Hz, 2H), 4.56-4.65 (m, 1H), 4.52 (s, 2H), 3.94-4.09 (m, 4H), 3.49-3.55 (m, 1H), 3.44-3.49 (m, 4H), 3.27 (d, J=13.4 Hz, 2H), 3.24 (s, 6H), 3.08 (s, 3H), 1.93 (d, J=9.9 Hz, 2H), 1.70-1.80 (m, 2H), 1.47-1.66 (m, 2H), 1.22-1.38 (m, 2H). MS (ES+): m/z 708.26 (100) [MH+]. HPLC: tR=3.61 min (ZQ3, polar—5 min).

Workup

  1. customThe title product was prepared
  2. concentrationThe reaction mixture concentrated
  3. custompurified by MDP [under basic conditions; ammonium bicarbonate basic buffer (pH 9)]

Sources & evidence

ORD record
ord-4a73cbed93674c06bfae4374c5e7b6f2
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

Loading…