Hydrochloric Acid → 4-Fluoro-2-(4-methyl-5-oxo-6-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)-4,5-dihydropyrazin-2-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl Acetate

HRID 1918858Notes

Reaction equation

HRID 1918858 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:18][C:19]3[C:24](=[O:25])[N:23]([CH3:26])[CH:22]=[C:21]([C:27]4[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([N:34]5[CH2:46][CH2:45][N:37]6[C:38]7[CH2:39][CH2:40][CH2:41][CH2:42][C:43]=7[CH:44]=[C:36]6[C:35]5=[O:47])[C:28]=4[CH2:48][O:49][C:50](=[O:52])[CH3:51])[N:20]=3)[CH:14]=2)[CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[C:50]([O:49][CH2:48][C:28]1[C:29]([N:34]2[CH2:46][CH2:45][N:37]3[C:38]4[CH2:39][CH2:40][CH2:41][CH2:42][C:43]=4[CH:44]=[C:36]3[C:35]2=[O:47])=[CH:30][C:31]([F:33])=[CH:32][C:27]=1[C:21]1[N:20]=[C:19]([NH:18][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH2:9][NH:8][CH2:17][CH2:16]3)[C:24](=[O:25])[N:23]([CH3:26])[CH:22]=1)(=[O:52])[CH3:51]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67016272tert-Butyl-6-(6-(2-(acetoxymethyl)-5-fluoro-3-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)phenyl)-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 670162104-Fluoro-2-(4-methyl-5-oxo-6-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)-4,5-dihydropyrazin-2-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl AcetateYield 99.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To the solution of 129a (360 mg 0.51 mmol) in DCM (30 mL) was added 3M HCl in dioxane (8 mL) at room temperature. The mixture was stirred at room temperature for 5 h. After the reaction was completed, the solvent was removed at reduced pressure to afford 129b as a yellow solid (310 mg, 99%).

Workup

  1. customthe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-1b150895eadc469fb1bee388cbe83f08
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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