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

HRID 511422Notes

Reaction equation

HRID 511422 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:31]=[CH:30][C:16]([CH2:17][P:18](=[O:29])([O:24][CH2:25][CH2:26][O:27][CH3:28])[O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:15][CH:14]=2)[N:3]=1.[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>>[OH:50][C@H:47]1[CH2:48][CH2:49][C@H:44]([C:36]2[CH:35]=[CH:34][C:33]([NH:32][C:2]3[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][N:5]=[C:4]([NH:12][C:13]4[CH:31]=[CH:30][C:16]([CH2:17][P:18](=[O:29])([O:24][CH2:25][CH2:26][O:27][CH3:28])[O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:15][CH:14]=4)[N:3]=3)=[C:41]3[C:37]=2[CH2:38][N:39]([CH3:43])[C:40]3=[O:42])[CH2:45][CH2:46]1

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-5038b57b115844529d695437c68e96fc
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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