Acetic Acid → HCID 178492265, compound

HRID 561930Notes

Reaction equation

CC1(C)CO[CH:5]([C:8]2[C:13]([O:14]COC)=[C:12]([O:18][CH3:19])[CH:11]=[CH:10][C:9]=2[NH:20][CH2:21][C@@H:22]([OH:33])[CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=2[CH3:32])OC1.Cl.[NH2:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][C:45]=1[NH2:46])[C:42](=[O:47])[N:41]([CH:48]1[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]1)[CH2:40]2.CC(O)=O>C1COCC1.CCO>[CH3:32][C:26]1[CH:27]=[C:28]([CH3:31])[CH:29]=[CH:30][C:25]=1[O:24][CH2:23][C@H:22]([OH:33])[CH2:21][NH:20][C:9]1[C:8]([C:5]2[NH:46][C:45]3[C:37](=[CH:38][C:39]4[CH2:40][N:41]([CH:48]5[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]5)[C:42](=[O:47])[C:43]=4[CH:44]=3)[N:36]=2)=[C:13]([OH:14])[C:12]([O:18][CH3:19])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (R)-1-[2-(5,5-dimethyl-[1,3]dioxan-2-yl)-4-methoxy-3-methoxymethoxy-phenylamino]-3-(2,4-dimethyl-phenoxy)-propan-2-ol (102 mg, 0.21 mmol) in THF (5.0 mL) was added 36% aqueous HCl (1.0 mL). After it was heated at 50° C. for 1.5 h, the reaction mixture was evaporated and the residue was mixed with 5,6-diamino-2-(1-methyl-piperidin-4-yl)-2,3-dihydro-isoindol-1-one (76 mg, 0.21 mmol) and AcOH (0.4 mL) in EtOH (8 mL). The mixture was stirred at the room temperature for 30 min, heated at 80° C. for 1.5 h, and evaporated to dryness. Chromatography of the residual crude with CH2Cl2/MeOH/28% aqueous NH4OH (40:10:1) afforded the title compound (13 mg, 10%). ESI-MS m/z 586.5 (MH+).

Workup

customthe reaction mixture was evaporated
temperatureheated at 80° C. for 1.5 h
customevaporated to dryness

Sources & evidence

ORD record: ord-a3098d75f94c4ac092963aa7c3125681
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063225B2

Reaction notes

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