Diisopropylethylamine → 9H-fluoren-9-ylmethyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}amino)-2-oxoethyl]carbamate

HRID 1504872노트

반응식

HRID 1504872 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[N:12]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.Cl[C:20](=[O:40])[CH2:21][NH:22][C:23](=[O:39])[O:24][CH2:25][CH:26]1[C:38]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2.C(N(C(C)C)CC)(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>CN(C=O)C.C(OCC)(=O)C>[C:8]([C:5]1[N:6]=[CH:7][C:2]([NH:1][C:20](=[O:40])[CH2:21][NH:22][C:23](=[O:39])[O:24][CH2:25][CH:26]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=3[C:33]3[C:38]2=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:3][C:4]=1[NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[N:12]=1)#[N:9]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 11758879Fmoc-Gly-ClHCID 867316535-Amino-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile

생성물 1

HCID 867317419H-fluoren-9-ylmethyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}amino)-2-oxoethyl]carbamate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-amino-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile (PrepEx 1.8) (100 mg, 0.418 mmol), 9H-fluoren-9-ylmethyl (2-chloro-2-oxoethyl)carbamate (264 mg, 0.835 mmol), and diisopropylethylamine (0.15 mL, 0.84 mmol) in DMF (3.2 mL) at 0° C. was added 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate, 0.29 mL, 0.50 mmol). The reaction mixture was stirred for 2 hours while warming to room temperature. The reaction mixture was diluted with ethyl acetate and washed with sodium hydroxide (1.0 M in water). The organics were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Dichloromethane (3 mL) was slowly added, and the precipitated solids were filtered and collected to afford 9H-fluoren-9-ylmethyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}amino)-2-oxoethyl]carbamate. MS ESI calc'd for C30H27N6O3 [M+H]+ 519. found 519. 1H NMR (500 MHz, DMSO-d6) δ 10.54 (s, 1H), 9.09 (s, 1H), 8.78 (d, J=2.0 Hz, 1H), 8.39 (d, J=2.1 Hz, 1H), 7.88 (d, J=7.5 Hz, 2), 7.75-7.65 (m, 3H), 7.40 (t, J=7.4 Hz, 2H), 7.31 (t, J=7.4 Hz, 2H), 6.65 (s, 1H), 6.61 (s, 1H), 4.29 (d, J=7.0 Hz, 2), 4.24-4.20 (m, 1H), 3.84 (d, J=6.1 Hz, 2H), 2.28 (s, 3H), 2.20 (s, 3H).

후처리

  1. washwashed with sodium hydroxide (1.0 M in water)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionDichloromethane (3 mL) was slowly added
  6. filtrationthe precipitated solids were filtered
  7. customcollected

출처 및 근거

ORD 기록
ord-cac2e8c48d514bac954b820e3ff40d37
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216173B2

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