Hydrochloric Acid → Hydrochloric Acid

HRID 510939Notes

Reaction equation

HRID 510939 reaction equation
C(OC([NH:8][CH:9]([C:11]1[C:12]([O:33][CH3:34])=[C:13]([CH:19]2[CH2:22][N:21]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:20]2)[C:14]([CH3:18])=[C:15]([Cl:17])[CH:16]=1)[CH3:10])=O)(C)(C)C.[ClH:35].O1CCOCC1>C(Cl)Cl>[NH2:8][CH:9]([C:11]1[C:12]([O:33][CH3:34])=[C:13]([CH:19]2[CH2:22][N:21]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:20]2)[C:14]([CH3:18])=[C:15]([Cl:17])[CH:16]=1)[CH3:10].[ClH:35]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86666852Benzyl 3-(3-{1-[(tert-butoxycarbonyl)amino]ethyl}-5-chloro-2-methoxy-6-methylphenyl)azetidine-1-carboxylate

Product 2

HCID 313Hydrochloric AcidHCID 86666851Benzyl 3-[3-(1-aminoethyl)-5-chloro-2-methoxy-6-methylphenyl]azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl 3-(3-{1-[(tert-butoxycarbonyl)amino]ethyl}-5-chloro-2-methoxy-6-methylphenyl)azetidine-1-carboxylate (0.45 g, 0.92 mmol, from Example 170, Step 3, chiral intermediate) and was treated with 4.0 M HCl in dioxane (2 mL, 8 mmol) in methylene chloride (6 mL) at room temperature for 2 hours. The reaction mixture was then stripped to dryness to give benzyl 3-{3-[1-aminoethyl]-5-chloro-2-methoxy-6-methylphenyl}azetidine-1-carboxylate as a HCl salt. LCMS calculated for C21H26ClN2O3 (M+H)+: m/z=389.2. found: 389.1. A mixture of the above HCl salt, 6-bromo-9H-purine (0.20 g, 1.0 mmol) and DIPEA (0.80 mL, 4.6 mmol) in ethanol (9 mL) was heated at 100° C. overnight. The mixture was concentrated and purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product (0.25 g, 55% in 2 steps). LCMS calculated for C26H28ClN6O3 (M+H)+: m/z=507.2. found: 507.1.

Sources & evidence

ORD record
ord-dd0fba84e95645888e9baf4a7670f089
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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