Diisopropylethylamine → HCID 178461868, compound

HRID 475250Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[C:5]([Cl:17])=[CH:4][N:3]=1.Cl.O1CCCCC1[N:25]1[C:29]2[CH:30]=[CH:31][C:32]([C@@H:34]([NH2:36])[CH3:35])=[CH:33][C:28]=2[N:27]=[CH:26]1.CCN(C(C)C)C(C)C>CCCCO>[NH:25]1[C:29]2[CH:30]=[CH:31][C:32]([C@@H:34]([NH:36][C:2]3[N:7]=[C:6]([NH:8][C:9]4[CH:13]=[C:12]([CH:14]5[CH2:16][CH2:15]5)[NH:11][N:10]=4)[C:5]([Cl:17])=[CH:4][N:3]=3)[CH3:35])=[CH:33][C:28]=2[N:27]=[CH:26]1

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of 57 (135 mg, 0.5 mmol) in n-BuOH (3 mL) in a microwave vial was added 126 (184 mg, 0.75 mmol), then DIPEA (0.26 mL, 1.5 mmol) was added dropwise. The vial was sealed with a rubber septa and heated in the microwave for 90 min at 160° C. The solvent was evaporated under reduced pressure and the crude residue was taken up in DCM (5 mL) and MeOH (5 mL) and the solvent was again concentrated in vacuo. The residue was diluted in DMF (2 mL) and filtered to remove any undissolved solids. The filtrate was concentrated in vacuo. The residue was purified by reverse phase HPLC to afford 13 mg (6%) of I-46.

Workup

customThe vial was sealed with a rubber septa
customThe solvent was evaporated under reduced pressure
concentrationMeOH (5 mL) and the solvent was again concentrated in vacuo
additionThe residue was diluted in DMF (2 mL)
filtrationfiltered
customto remove any undissolved solids
concentrationThe filtrate was concentrated in vacuo
customThe residue was purified by reverse phase HPLC
customto afford 13 mg (6%) of I-46

Sources & evidence

ORD record: ord-ef8f328a0d1c4da49779398349c8fc62
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

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