Triethylamine → HCID 86636517, compound

HRID 1513451Notes

Reaction equation

Cl.[C:2]([O:6][C:7]([N:9]1[CH2:12][CH:11]([CH2:13][NH2:14])[CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].CCN(CC)CC.[Cl:22][C:23]1[N:28]=[C:27](Cl)[N:26]=[C:25]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:24]=1>C1COCC1>[C:2]([O:6][C:7]([N:9]1[CH2:12][CH:11]([CH2:13][NH:14][C:27]2[N:28]=[C:23]([Cl:22])[N:24]=[C:25]([N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[N:26]=2)[CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the 3-aminomethyl-azetidine-1-carboxylic acid tert-butyl ester HCl salt (945 mg, 4.24 mmol) and NEt3 (856 mg, 8.48 mmol) in THF (10 mL) at 0° C. was added a suspension of 2,4-dichloro-6-morpholin-4-yl-[1,3,5]triazine (996 mg, 4.24 mmol) at 0° C. The reaction mixture was stirred for another 1 hr at 0° C. and allowed to warm to 20° C. and stirred for 1-4 hrs to drive the reaction to completion. Silica gel (20 g) was added to the reaction mixture and the solvent was removed so that product was adsorbed on the silica gel. The silica gel plug was placed on top of a column to purify by flash chromatography using CH2Cl2/MeOH/NH3 (20:1:01) eluent. After unifying the product fraction, and evaporation of solvent, (750 mg, 46% yield) product was obtained as yellow solid; MS (ESI) m/z 385

Workup

temperatureto warm to 20° C.
stirringstirred for 1-4 hrs
customthe reaction to completion
additionSilica gel (20 g) was added to the reaction mixture
customthe solvent was removed so that product
customto purify by flash chromatography
customthe product fraction, and evaporation of solvent

Sources & evidence

ORD record: ord-02662a9d5bd049ef976fbaf35f1841a4
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217036B2

Reaction notes

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