Benzoic Acid → HCID 58405423, compound

HRID 44852Notes

Reaction equation

HRID 44852 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:17]=[CH:16][C:15]2[N:14]([CH3:18])[C:13](=[O:19])[C@@H:12]([CH2:20][CH3:21])[N:11]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[C:10]=2[N:9]=1.[C:27](O)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1.O>[CH:22]1([N:11]2[C:10]3[N:9]=[C:8]([C:7]4[CH:6]=[CH:5][N:4]=[CH:3][C:2]=4[NH:1][C:27](=[O:34])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:17]=[CH:16][C:15]=3[N:14]([CH3:18])[C:13](=[O:19])[C@H:12]2[CH2:20][CH3:21])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58405310HCID 58405310, compound

Product 1

HCID 58405423HCID 58405423, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (R)-2-(3-aminopyridin-4-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 91, 1 eq), benzoic acid (3 eq), HATU (3 eq), and DIPEA (4 eq) in dry THF under Ar was stirred at 90° C. for 18 h. The mixture was cooled to rt and water was added and extracted with EtOAc. The organic layer was dried with Na2SO4, concentrated and the residue was purified by silica gel column to give the title compound. LCMS (0.05% TFA): 457.2 m/z (M+H)+; 1H-NMR (DMSO-d6, 500 MHz): δ: 13.75 (s, 1H), 10.00 (bs, 1H), 8.55 (bs, 1H), 8.39 (d, 1H, J=5.0 Hz), 8.31 (s, 1H), 8.07 (m, 2H), 7.69 (m, 3H), 4.46 (m, 1H), 4.39 (m, 1H), 3.38 (s, 3H), 2.02-1.63 (m, 10H), 0.77 (t, 3H, J=7.5 Hz).

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried with Na2SO4
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel column

Sources & evidence

ORD record
ord-b51b6dd3662346f18fd3940c7f42fef3
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

Loading…