Acetonitrile → HCID 24894758, compound

HRID 419227Notes

Reaction equation

ClC1N=C(NC(C2C=CC3C(=CC=CC=3)C=2)C)N=C(N)N=1.C(#N)C.C(=O)([O-])[O-].[Na+].[Na+].[NH2:31][CH:32]([CH2:36][N:37]1[CH:41]=[CH:40][C:39]([C:42]2[N:47]=[C:46]([NH2:48])[N:45]=[C:44]([NH:49][CH:50]([C:52]3[CH:61]=[CH:60][C:59]4[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=4)[CH:53]=3)[CH3:51])[N:43]=2)=[N:38]1)[C:33]([OH:35])=[O:34]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[NH2:31][C@@H:32]([CH2:36][N:37]1[CH:41]=[CH:40][C:39]([C:42]2[N:47]=[C:46]([NH2:48])[N:45]=[C:44]([NH:49][C@@H:50]([C:52]3[CH:61]=[CH:60][C:59]4[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=4)[CH:53]=3)[CH3:51])[N:43]=2)=[N:38]1)[C:33]([OH:35])=[O:34]

Participants

Conditions

Temperature: 150 °C

Procedure

6-Chloro-N-[1-naphthalen-2-yl-ethyl]-[1,3,5]triazine-2,4-diamine (30 mg, 0.1 mmol), 2-boc-protected amino-3-{3-[4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-propionic acid (50 mg, 0.15 mmol), 1 ml of acetonitrile, and 0.7 ml of water. Aqueous sodium carbonate (0.3 ml and 1N) was added to a microwave vial, followed by 5 mol percent of dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 150° C. for 5 minutes with microwave. After cooling, the reaction mixture was evaporated to dryness, the residue was dissolved in 2.5 ml of methanol, and then was purified with Prep-LC to give 6.8 mg of boc protected 2-amino-3-{3-[4-amino-6-(1-naphthalen-2-yl-ethylamino)[1,3,5]triazin-2-yl]-pyrazol-1-yl}proionic acid.

Workup

customThe reaction vessel was sealed
temperatureAfter cooling
customthe reaction mixture was evaporated to dryness
dissolutionthe residue was dissolved in 2.5 ml of methanol
customwas purified with Prep-LC
customto give 6.8 mg of boc

Sources & evidence

ORD record: ord-e9e6f5106b0c4e2da4e2593ee4a23e1d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093291B2

Reaction notes

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