Triethylamine → HCID 57791804, compound

HRID 1091754Notes

Reaction equation

HRID 1091754 reaction equation
Cl.[C:2]([O:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[O:20]=[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH2:31][C:32]2[CH:37]=[CH:36][N:35]=[C:34]([C:38](O)=[O:39])[CH:33]=2)=[N:23][NH:22]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[C:2]([O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:38]([C:34]2[CH:33]=[C:32]([CH2:31][C:24]3[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:21](=[O:20])[NH:22][N:23]=3)[CH:37]=[CH:36][N:35]=2)=[O:39])[CH2:9][CH2:8]1)([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21734650HCID 21734650, compoundHCID 59767737HCID 59767737, compound

Product 1

HCID 57791804HCID 57791804, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 4-tert-butoxypiperidine hydrochloride (227 mg, 1.17 mmol) and triethylamine (0.327 mL, 2.35 mmol) in N,N-dimethlformamide (3 mL) was added in one portion to a stirred solution of 4-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)picolinic acid (5) (300 mg, 1.07 mmol), Triethylamine (0.327 mL, 2.35 mmol) and O-Benzotriazol-1-yl-N,N,N′,N′-tetra-methyluronium hexafluorophosphate (607 mg, 1.60 mmol) in N,N-dimethlformamide (3 mL) at 25° C. The resulting solution was stirred at 25° C. for 4 hours, then The crude mixture was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 30 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness and lyophilised to afford the desired compound as a solid (250 mg, 55.7% yield); 1H NMR (400.132 MHz, DMSO) δ 1.15 (9H, s), 1.25-1.40 (2H, m), 1.56-1.63 (1H, m), 1.71-1.79 (1H, m), 3.08-3.23 (2H, m), 3.44-3.50 (1H, m), 3.71-3.78 (1H, m), 4.01-4.08 (1H, m), 4.40 (2H, s), 7.39 (1H, dd), 7.48-7.49 (1H, m), 7.83-7.87 (1H, m), 7.90 (1H, td), 7.94-7.97 (1H, m), 8.28 (1H, dd), 8.46-8.48 (1H, m), 12.60 (1H, s); m/z (LC-MS, ESI+), RT=1.67 (M+H 421.5).

Workup

  1. customThe crude mixture was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 30 mm diameter, 100 mm length)
  2. additionFractions containing the desired compound
  3. customwere evaporated to dryness

Sources & evidence

ORD record
ord-e62e8fcf2fdd442cad4cd70ea24f366c
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

Loading…