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Triethylamine → HCID 178509596, compound

HRID 1524866
Notes
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Reaction equation

HRID 1524866 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]([OH:17])=O)[NH:12][CH:13]=2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH2:59][C:60]1[CH:68]=[CH:67][C:63]([C:64]([NH2:66])=[O:65])=[CH:62][CH:61]=1>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([CH:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]([NH:59][C:60]3[CH:68]=[CH:67][C:63]([C:64]([NH2:66])=[O:65])=[CH:62][CH:61]=3)=[O:17])[NH:12][CH:13]=2)=[CH:7][CH:8]=1)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 760794-AminobenzamideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178509597HCID 178509597, compound

Product 1

HCID 178509596HCID 178509596, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

The acid from Example 59 Part A (100 mg, 0.32 mmol), triethylamine (150 μL, 1.2 mmol), and BOP reagent (210 mg, 0.48 mmol) were dissolved in THF (9 mL). The mixture was stirred at rt for 15 min and 4-aminobenzamide (47 mg, 0.35 mmol) was added. The resulting mixture was heated at 70° C. under N2 for 1 h. The mixture was concentrated and then re-dissolved in EtOAc. It was washed with water and brine, dried over Na2SO4, concentrated, and purified by flash chromatography (silica gel, EtOAc/hexane) to give 45 mg of the desired product (32%). MS 436.3 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated at 70° C. under N2 for 1 h
  2. concentrationThe mixture was concentrated
  3. dissolutionre-dissolved in EtOAc
  4. washIt was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by flash chromatography (silica gel, EtOAc/hexane)

Sources & evidence

ORD record
ord-f4870750af4b40f8aa40232e5a631679
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09079860B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes