Hydrochloric Acid → HCID 86666869, compound

HRID 510952Notes

Reaction equation

HRID 510952 reaction equation
C(OC([NH:8][CH:9]([C:11]1[C:12]([O:33][CH2:34][CH3:35])=[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.Cl.O1CCOCC1.C(Cl)Cl>>[ClH:17].[NH2:8][CH:9]([C:11]1[C:12]([O:33][CH2:34][CH3:35])=[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]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 86666867HCID 86666867, compound

Product 1

HCID 86666869HCID 86666869, compound

Procedure

Benzyl 3-(3-{1-[(tert-butoxycarbonyl)amino]ethyl}-5-chloro-2-ethoxy-6-methylphenyl)azetidine-1-carboxylate (65 mg, 0.13 mmol, second peak from chiral separation in previous step) was treated with 4.0 M HCl in dioxane (0.4 mL, 2 mmol) in methylene chloride (0.4 mL, 6 mmol) at room temperature for 2 hours. The reaction mixture was evaporated to dryness to give benzyl 3-[3-[1-aminoethyl]-5-chloro-2-ethoxy-6-methylphenyl]azetidine-1-carboxylate hydrochloride. LCMS calculated for C22H28ClN2O3 (M+H)+: m/z=4012. found: 403.1. A mixture of the above HCl salt, 6-bromo-9H-purine (31 mg, 0.16 mmol) and DIPEA (0.11 mL, 0.65 mmol) in ethanol (1 mL) was heated at 100° C. overnight. The mixture was diluted with sat. NaHCO3 solution, extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give the desired product (83 mg). LCMS calculated for C27H30ClN6O3 (M+H)+: m/z=521.2. found: 521.1.

Workup

  1. customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-8d9f1fe4585d47b0934767350ecff24b
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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