Diphenylacetic Acid → HCID 178522377, compound

HRID 1470316Notes

Reaction equation

HRID 1470316 reaction equation
[NH2:1][C:2]1[C:3]([OH:14])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:6][CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[C:46]1([CH:52]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:53](O)=[O:54])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CC#N.O>[OH:14][C:3]1[C:2]([NH:1][C:53](=[O:54])[CH:52]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[CH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:4]=1

Participants

7

Reactant 4

HCID 8333Diphenylacetic AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178508021HCID 178508021, compound

Product 1

HCID 178522377HCID 178522377, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-amino-2-(pyridin-2-yl)pyrimidin-4-ol (10-e) (120 mg, 0.64 mmol) in MeCN (5 ml) were added HATU (254 mg, 0.67 mmol), Et3N (130 mg, 1.28 mmol) and 2,2-diphenylacetic acid (135 mg, 0.64 mmol). The resulting mixture was stirred at room temperature for 1 hour. Then the mixture was diluted with water and followed by extraction with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified by prep-HPLC to provide compound 10-1. 1H NMR (DMSO-d6, 300 MHz): δ 12.50 (br, 1H), 9.85 (br, 1H), 8.73 (m, 2H), 8.10 (m, 1H), 8.00 (m, 1H), 7.60 (m, 1H), 7.35 (m, 10H), 5.75 (s, 1H). (M+H)+=383.2.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-be680e1d5000412e8dff822067df6f01
Source dataset
uspto-grants-2015_04
Patent number
US09006433B2

Reaction notes

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