Triethylamine → HCID 57791769, compound

HRID 1091722Notes

Reaction equation

HRID 1091722 reaction equation
C(N(CC)CC)C.[O:8]=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([C:26]([OH:28])=O)[CH:21]=2)=[N:11][NH:10]1.Cl.[CH:30]1([O:35][CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:34][CH2:33][CH2:32][CH2:31]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CC(N(C)C)=O>[CH:30]1([O:35][CH:36]2[CH2:41][CH2:40][N:39]([C:26]([C:22]3[CH:21]=[C:20]([CH2:19][C:12]4[C:13]5[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=5)[C:9](=[O:8])[NH:10][N:11]=4)[CH:25]=[CH:24][N:23]=3)=[O:28])[CH2:38][CH2:37]2)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 470028554-(cyclopentyloxy)piperidine hydrochlorideHCID 59767737HCID 59767737, compound

Product 1

HCID 57791769HCID 57791769, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
20 °C

Procedure

Triethylamine (0.452 ml, 3.24 mmol) was added in one portion to 4-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)picolinic acid (5) (304 mg, 1.08 mmol), 4-(cyclopentyloxy)piperidine hydrochloride (183 mg, 1.08 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetra-methyluronium hexafluorophosphate (533 mg, 1.41 mmol) in DMA (3 ml) at 20° C. under air. The resulting mixture was stirred at 20° C. for 3 days. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 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 to afford the desired material as a white solid (39 mg, 8.3% yield); 1H NMR (400.132 MHz, DMSO) δ 1.28-1.74 (11H, m), 1.82-1.88 (1H, m), 3.08-3.14 (1H, m), 3.20-3.27 (1H, m), 3.44-3.49 (1H, m), 3.53-3.59 (1H, m), 3.96-4.05 (2H, m), 4.40 (2H, s), 7.39 (1H, d), 7.49 (1H, s), 7.83-7.96 (3H, m), 8.28 (1H, d), 8.47 (1H, d), 12.60 (1H, s); m/z (LC-MS, ESI+), RT=1.88 (M+H 433.1).

Workup

  1. customThe crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length)
  2. additionFractions containing the desired compound
  3. customwere evaporated to dryness

Sources & evidence

ORD record
ord-cb367a03f93f459d9d47aba04d58715c
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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