4-Methylmorpholine → HCID 67092312, 화합물

HRID 2074101노트

반응식

HRID 2074101 반응식
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[N:11]([CH:12]3[CH2:15][NH:14][CH2:13]3)[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.[NH:52]1[CH:56]=[CH:55][N:54]=[C:53]1[C:57](O)=[O:58]>CN(C=O)C.CCOCC>[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[N:11]([CH:12]3[CH2:13][N:14]([C:57]([C:53]4[NH:52][CH:56]=[CH:55][N:54]=4)=[O:58])[CH2:15]3)[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

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5743211H-Imidazole-2-carboxylic acidHCID 67092285HCID 67092285, 화합물

생성물 1

HCID 67092312HCID 67092312, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 4-(5-(4-fluorobenzyl)-1-(azetidin-3-yl)-1H-pyrazol-3-yl)pyridine (85 mg, 0.28 mmol) in DMF (3 mL) was added HOBt (45 mg, 0.33 mmol), EDCI (64 mg, 0.33 mmol), NMM (76 μL, 0.69 mmol) followed by imidazole-2-carboxylic acid (34 mg, 0.30 mmol) and the mixture stirred for 16 hours at room temperature. The volatiles were removed in vacuo and the residue purified directly by Biotage flash chromatography, eluting with 2-6% MeOH/DCM to yield a clear gum. Ether was added (5 mL) and the mix sonicated to give a white precipitate that was filtered off, washed with ether and dried in-vacuo to yield the title compound as a white solid, 78 mg, 70%. 1H NMR (400 MHz, DMSO-D6) δ ppm 13.04-13.12 (m, 1 H), 8.54 (d, 2 H), 7.74 (d, 2 H), 7.25-7.32 (m, 2 H), 7.18 (t, 2 H), 7.03-7.12 (m, 1 H), 6.66 (s, 1 H), 5.33-5.46 (m, 1 H), 4.77-4.92 (m, 2 H), 4.26-4.36 (m, 2 H), 4.12 (s, 2 H); m/z (APCI+) for C22H19N6FO 403.1 (M+H)+.

후처리

  1. customThe volatiles were removed in vacuo
  2. customthe residue purified directly by Biotage flash chromatography
  3. washeluting with 2-6% MeOH/DCM
  4. customto yield a clear gum
  5. customthe mix sonicated
  6. customto give a white precipitate that
  7. filtrationwas filtered off
  8. washwashed with ether
  9. customdried in-vacuo

출처 및 근거

ORD 기록
ord-e53f822b039c4820926e4064a6ac9be0
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919488B2

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