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Acetonitrile → HCID 24894758, compound

HRID 1958578
Notes
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Reaction equation

HRID 1958578 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 66653069HCID 66653069, compoundHCID 74338134HCID 74338134, compound

Product 1

HCID 24894758HCID 24894758, compound

Reagents, catalysts & solvents 2

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

6-Chloro-N-[1-naphthalen-2yl-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

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

Sources & evidence

ORD record
ord-2e60cf95c51a446a88c71bb0588b03ca
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08410121B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes