Triethylamine → HCID 56650038, compound

HRID 1464964Notes

Reaction equation

HRID 1464964 reaction equation
Cl.Cl.[CH2:3]([O:7][C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[N:11]=[CH:10][N:9]=1)[CH:4]([CH3:6])[CH3:5].[OH:20][C@H:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:22](O)=[O:23].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[OH:20][C@H:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:22]([N:17]1[CH2:18][CH2:19][N:14]([C:12]2[CH:13]=[C:8]([O:7][CH2:3][CH:4]([CH3:6])[CH3:5])[N:9]=[CH:10][N:11]=2)[CH2:15][CH2:16]1)=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11914(-)-Mandelic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66747984HCID 66747984, compound

Product 1

HCID 56650038HCID 56650038, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-isobutoxy-6-(piperazin-1-yl)pyrimidine dihydrochloride (30 mg, 0.097 mmol), (R)-2-hydroxy-2-phenylacetic acid (15 mg, 0.097 mmol), and triethylamine (0.07 mL, 0.49 mmol) in DMF was added HBTU (48 mg, 0.13 mmol), and the mixture was stirred at rt for 1 h. Then the mixture was poured onto water (3 mL), and the aqueous layer was extracted with dichloromethane (three times). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative LC-MS to give 7.2 mg (15% yields) of the title compound.

Workup

  1. additionThen the mixture was poured onto water (3 mL)
  2. extractionthe aqueous layer was extracted with dichloromethane (three times)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative LC-MS
  6. customto give

Sources & evidence

ORD record
ord-5033453dadd645b88de9334a03d231c3
Source dataset
uspto-grants-2015_04
Patent number
US08999974B2

Reaction notes

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