Triethylamine → HCID 178476962, compound

HRID 1525245Notes

Reaction equation

HRID 1525245 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([OH:18])=O)=[CH:11][CH:10]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:56][C:57]1[C:58]([OH:68])=[N:59][C:60]([N:63]2[CH:67]=[CH:66][CH:65]=[N:64]2)=[N:61][CH:62]=1>CC#N>[OH:68][C:58]1[C:57]([NH:56][C:16](=[O:18])[CH:15]([C:12]2[CH:11]=[CH:10][C:9]([P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:3][CH2:1][CH3:2])=[CH:14][CH:13]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:62][N:61]=[C:60]([N:63]2[CH:67]=[CH:66][CH:65]=[N:64]2)[N:59]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 894624812-(4-(Diethoxyphosphoryl)phenyl)-2-phenylacetic acid2×HCID 178508031HCID 178508031, compound

Product 1

HCID 178476962HCID 178476962, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-(Diethoxyphosphoryl)phenyl)-2-phenylacetic acid, 14-f, (1.18 g, 3.4 mmol), HATU (1.86 g, 4.9 mmol) and triethylamine (989 mg, 9.8 mmol) in CH3CN (20 mL) was added 5-amino-2-(1H-pyrazol-1-yl)pyrimidin-4-ol (11-e, 577 mg, 3.30 mmol). The mixture was stirred at room temperature overnight and concentrated. The residue was taken up in EA and water. The aqueous layer was extracted with EA. The combined layers were washed with brine, dried over Na2SO4, and concentrated to give the crude product of 14-1 which was purified by pre-HPLC (766 mg, 45%). 1H NMR (300 MHz, DMSO-d6) δ1.18-1.23 (m, 6H), 3.92-4.03 (m, 4H), 6.64 (s, 1H), 7.25-7.35 (m, 6H), 7.47-7.51 (m, 2H), 7.64-7.71 (m, 2H), 7.97 (s, 1H), 8.61-8.52 (m, 1H), 8.63 (br s, 1H); LC-MS: (M+H)+ 508.

Workup

  1. concentrationconcentrated
  2. extractionThe aqueous layer was extracted with EA
  3. washThe combined layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-89efca8fe81448b589eb8ce1fbbe919f
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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