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Triethylamine → HCID 57791833, compound

HRID 1091720
Notes
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Reaction equation

HRID 1091720 reaction equation
C(N(CC)CC)C.F[C:9]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22](=[O:29])[NH:21][N:20]=2)=[CH:14][C:10]=1[C:11]([OH:13])=O.Cl.[CH:31]1([O:36][CH:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH2:35][CH2:34][CH2:33][CH2:32]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:31]1([O:36][CH:37]2[CH2:42][CH2:41][N:40]([C:11]([C:10]3[CH:14]=[C:15]([CH:16]=[CH:17][CH:9]=3)[CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22](=[O:29])[NH:21][N:20]=3)=[O:13])[CH2:39][CH2:38]2)[CH2:35][CH2:34][CH2:33][CH2:32]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 248117402-Fluoro-5-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acidHCID 470028554-(cyclopentyloxy)piperidine hydrochloride

Product 1

HCID 57791833HCID 57791833, compound
Yield 39.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
20 °C

Procedure

Triethylamine (0.298 ml, 2.14 mmol) was added in one portion to 3-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid (1b) (200 mg, 0.71 mmol), 4-(cyclopentyloxy)piperidine hydrochloride (121 mg, 0.71 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetra-methyluronium hexafluorophosphate (352 mg, 0.93 mmol) in DMA (2 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 (120 mg, 39% yield); 1H NMR (400.132 MHz, DMSO) δ 1.22-1.86 (11H, m), 3.00-3.20 (2H, m), 3.25-3.43 (2H, m), 3.52-3.56 (1H, m), 3.91-4.05 (2H, m), 4.35 (2H, s), 7.20 (1H, d), 7.31 (1H, s), 7.34-7.40 (2H, m), 7.80-7.89 (2H, m), 7.96 (1H, d), 8.26 (1H, d), 12.57 (1H, s); m/z (LC-MS, ESI+), RT=2.18 (M+H 432.1)

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-932a18cad1c64daeb5c53af6354c703d
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129380B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes