Hydrochloric Acid → HCID 24950748, compound

HRID 625081Notes

Reaction equation

HRID 625081 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@@H:10]([NH:32]C(=O)OC(C)(C)C)[C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[C:20]4[CH:27]([CH2:28][CH3:29])[S:26](=[O:31])(=[O:30])[CH2:25][C:21]=4[N:22]=[CH:23][N:24]=3)[CH2:15][CH2:14]2)=[O:12])=[CH:5][C:4]=1[F:40]>O1CCOCC1.C(Cl)Cl.CO>[NH2:32][C@H:10]([CH2:9][C:6]1[CH:7]=[CH:8][C:3]([Cl:2])=[C:4]([F:40])[CH:5]=1)[C:11]([N:13]1[CH2:14][CH2:15][N:16]([C:19]2[C:20]3[CH:27]([CH2:28][CH3:29])[S:26](=[O:30])(=[O:31])[CH2:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH2:17][CH2:18]1)=[O:12]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86675335HCID 86675335, compound

Product 1

HCID 24950748HCID 24950748, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

HCl in dioxane (4M, 2 mL) was added to a solution of tert-butyl (2R)-3-(4-chloro-3-fluorophenyl)-1-(4-(5-ethyl-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate (0.005 g, 0.009 mmol) in DCM (2 mL) and MeOH (1 mL). The mixture was stirred at room temperature for 5 hours. The solvent was removed to afford (2R)-2-amino-3-(4-chloro-3-fluorophenyl)-1-(4-(5-ethyl-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one as the HCl salt (4 mg, 97%). LCMS: 482.1 [M+H+] (APCI+).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-2c0e6d145526454d813590c55c7f95a1
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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