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Dimethylamine → HCID 11676128, compound

HRID 900320
Notes
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Reaction equation

HRID 900320 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[CH2:20][N:21]3[CH2:26][CH2:25][C@@H:24]([NH:27]C(=O)OCC=C)[C@H:23]([C:34](=[O:37])[NH:35][CH3:36])[CH2:22]3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.N(C)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:27][C@@H:24]1[CH2:25][CH2:26][N:21]([CH2:20][C:18]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:19]=2[C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:11][CH:12]=[N:13]3)[CH2:22][C@H:23]1[C:34]([NH:35][CH3:36])=[O:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 674DimethylamineHCID 58711726HCID 58711726, compound

Product 1

HCID 11676128HCID 11676128, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 15E (27 mg, 0.054 mmol) in THF (3 ml) was degassed and purged with N2. To this was added 2N Me2NH in THF (95 μl, 0.19 mmol), followed by Pd(PPh3)4 (9 mg, 0.0078 mmol). The mixture was stirred at room temperature for 1.5 h. Concentration in vacuo followed by purification using preparative HPLC gave, after concentration and lyophilization, a TFA salt of 15F (20.3 mg, 70%) as a solid. The compound has an analytical HPLC retention time=1.307 min (Chromolith SpeedROD column 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA over 4 minutes, 4 mL/min, monitoring at 254 nm) and a LC/MS M++H=421+.

Workup

  1. custompurged with N2
  2. concentrationConcentration in vacuo
  3. customfollowed by purification
  4. customgave
  5. concentrationafter concentration and lyophilization
  6. customan analytical HPLC retention time=1.307 min (Chromolith SpeedROD column 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA over 4 minutes, 4 mL/min, monitoring at 254 nm)

Sources & evidence

ORD record
ord-07a4f55bc1f1474190699e3ca704c1fe
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07358256B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes