Hydrochloric Acid → HCID 44624273, compound

HRID 2274084Notes

Reaction equation

HRID 2274084 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:32]=[CH:31][C:10]([CH2:11][O:12][C:13]2[CH:21]=[CH:20][C:19]3[NH:18][C:17]4[CH:22]([CH2:25][C:26]([O:28]CC)=[O:27])[CH2:23][CH2:24][C:16]=4[C:15]=3[CH:14]=2)=[CH:9][CH:8]=1.[OH-].[Li+].Cl>O1CCOCC1>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:32]=[CH:31][C:10]([CH2:11][O:12][C:13]2[CH:21]=[CH:20][C:19]3[NH:18][C:17]4[CH:22]([CH2:25][C:26]([OH:28])=[O:27])[CH2:23][CH2:24][C:16]=4[C:15]=3[CH:14]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67211458HCID 67211458, compound

Product 1

HCID 44624273HCID 44624273, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of ethyl 2-(7-(4-(pyrazin-2-yl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (15 mg, 0.035 mmol) in dioxane (1 mL) was added 1 M lithium hydroxide solution (0.175 mL, 0.175 mmol). The reaction mixture was stirred at room temperature for 5 h and acidified with HCl solution. The mixture was purified by HPLC to give the title compound (8 mg) as a pinkish solid. LCMS m/z=400.4 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 2.04-2.12 (m, 1H), 2.35 (dd, J=16.0 and 9.0 Hz, 1H), 2.62-2.75 (m, 4H), 3.44-3.50 (m, 1H), 5.17 (s, 2H), 6.74 (dd, J=8.7 and 2.4 Hz, 1H), 6.95 (d, J=2.4 Hz, 1H), 7.21 (d, J=8.7 Hz, 1H), 7.62 (d, J=8.2 Hz, 2H), 8.15 (d, J=8.3 Hz, 2H), 8.61 (d, J=2.5 Hz, 1H), 8.72 (dd, J=2.3 and 1.6 Hz, 1H), 9.26 (d, J=1.5 Hz, 1H), 10.47 (s, 1H), 12.20 (s, 1H).

Workup

  1. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-8a0c422d35f04e429ee4652f2fffb4b9
Source dataset
uspto-grants-2015_09
Patent number
US09126932B2

Reaction notes

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