Hydrochloric Acid → HCID 69002049, compound

HRID 1909625Notes

Reaction equation

HRID 1909625 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:29]>O1CCOCC1>[ClH:29].[C:25]1([CH3:28])[CH:24]=[CH:23][C:22]([O:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[CH:16][CH:17]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69000229HCID 69000229, compound

Product 1

HCID 69002049HCID 69002049, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following the general procedure for Example 13 (step 4), the product from step 3 (0.39 g, 1.02 mmol) was treated with 4M HCl in dioxane (6 mL) to afford the title compound (0.12 g, 67%) as an off-white solid; 1H NMR (400 MHz, DMSO-d6) 1.74 (m, 1H), 1.94 (m, 2H), 2.11 (m, 1H), 2.27 (s, 3H), 3.21 (m, 2H), 3.88 (m, 1H), 4.13 (m, 1H), 4.22 (dd, J1=3.8 Hz, J2=10.8 Hz, 1H), 6.83 (d, J=8.4 Hz, 2H), 6.98 (m, 4H), 7.16 (d, J=8.4 Hz, 2H), 9.11 (br s, 1H), 9.67 (br s, 1H); MS (m/z) 284.4 (M+1); LC (98.8%); HPLC (99.3%).

Sources & evidence

ORD record
ord-7f4a4739b43e439b9221fbb73de5c7f6
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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