4-Methylmorpholine → HCID 67092195, compound

HRID 2074083Notes

Reaction equation

HRID 2074083 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13](O)=[O:14])[N:10]=[C:9]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:8]=2)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CN1CCOCC1.Cl.[NH:53]1[CH2:58][CH2:57][CH:56]([N:59]2[CH2:63][CH2:62][CH2:61][C:60]2=[O:64])[CH2:55][CH2:54]1>CC(N(C)C)=O>[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]([N:53]3[CH2:54][CH2:55][CH:56]([N:59]4[CH2:63][CH2:62][CH2:61][C:60]4=[O:64])[CH2:57][CH2:58]3)=[O:14])[N:10]=[C:9]([C:16]3[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=3)[CH:8]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 230188401-(Piperidin-4-yl)pyrrolidin-2-one--hydrogen chloride (1/1)HCID 670925255-[(4-fluorophenyl)methyl]-3-(4-pyridinyl)-1H-Pyrazole-1-acetic acid

Product 1

HCID 67092195HCID 67092195, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of [5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetic acid (164 mg, 0.53 mmol) in DMA (3 mL) at room temperature was added HOBt (78 mg, 0.58 mmol), EDCI (111 mg, 0.58 mmol), NMM (0.20 mL, 1.84 mmol) and 1-piperidin-4-ylpyrrolidin-2-one hydrochloride (150 mg, 0.73 mmol) and the mixture sonicated to a fine suspension and stirred for 64 hours at room temperature. The volatiles were removed under high vacuum and the residue partitioned between EtOAc (70 mL) and water (25 mL). The aqueous layer was removed and the organics washed with NaHCO3 (30 mL), brine (30 mL), dried over MgSO4, filtered and stripped to yield the title compound as an off-white solid, 123 mg, 51%. 1H NMR (400 MHz, DMSO-D6) δ ppm 8.51-8.54 (2 H, m), 7.64-7.69 (2 H, m), 7.25-7.35 (2 H, m), 7.11-7.21 (2 H, m), 6.53 (1 H, s), 5.11-5.28 (2 H, m), 4.37 (1 H, d, J=13.14 Hz), 3.90-4.05 (4 H, m), 3.23-3.31 (2 H, m), 3.08-3.20 (1 H, m), 2.57-2.70 (1 H, m), 2.22 (2 H, t, J=8.08 Hz), 1.84-1.95 (2 H, m), 1.40-1.73 (4 H, m); m/z (APCI+) for C26H28N5O2F 462.2 (M+H)+.

Workup

  1. customthe mixture sonicated to a fine suspension
  2. customThe volatiles were removed under high vacuum
  3. customthe residue partitioned between EtOAc (70 mL) and water (25 mL)
  4. customThe aqueous layer was removed
  5. washthe organics washed with NaHCO3 (30 mL), brine (30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ad1bf9992bed4edfbb4c463924a42a13
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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