Diisopropylethylamine → HCID 68735841, compound

HRID 1091705Notes

Reaction equation

HRID 1091705 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[NH:14][N:13]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.[CH:56]1([O:60][CH:61]2[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]2)[CH2:59][CH2:58][CH2:57]1>CN(C)C=O>[CH:56]1([O:60][CH:61]2[CH2:66][CH2:65][N:64]([C:4]([C:3]3[CH:7]=[C:8]([CH:9]=[CH:10][C:2]=3[F:1])[CH2:11][C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15](=[O:22])[NH:14][N:13]=3)=[O:5])[CH2:63][CH2:62]2)[CH2:59][CH2:58][CH2:57]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 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 54594082HCID 54594082, compound

Product 1

HCID 68735841HCID 68735841, compoundYield 5.82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid (1b) (0.20 g, 0.67 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetra-methyluronium hexafluorophosphate (0.381 g, 1.01 mmol) were added to N,N-dimethylformamide (30 mL), and to this was added N-ethyl-N-isopropylpropan-2-amine (0.179 mL, 1.01 mmol) and then 4-cyclobutoxypiperidine (14) (0.104 g, 0.67 mmol). The reaction was stirred for 2 hours before being purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 21 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 compound as a white solid (0.017 g, 5.82%); 1H NMR (400.132 MHz, CDCl3) δ 1.56-1.44 (2H, m), 1.72-1.64 (2H, m), 2.00-1.84 (4H, m), 2.23-2.14 (2H, m), 3.14-3.04 (1H, m), 3.48-3.41 (2H, m), 3.58-3.52 (1H, m), 4.00 (1H, quintet), 4.10-4.03 (1H, m), 4.26 (2H, s), 7.01 (1H, t), 7.31-7.24 (2H, m), 7.77-7.70 (3H, m), 8.47-8.44 (1H, m), 9.90 (1H, s); m/z (LC-MS, ESI+), RT=2.15 (M+H 436).

Workup

  1. custombefore being purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 21 mm diameter, 100 mm length)
  2. additionFractions containing the desired compound
  3. customwere evaporated to dryness

Sources & evidence

ORD record
ord-aef8e5083e3546739a8b17b77cac93c9
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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