4-Methylmorpholine → HCID 67092195, 화합물

HRID 2074083노트

반응식

HRID 2074083 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

HCID 67092195HCID 67092195, 화합물

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-ad1bf9992bed4edfbb4c463924a42a13
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919488B2

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