Hydrochloric Acid → 2-(3,5-Dimethyl-4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-5,7-diisopropoxypyrido[2,3-d]pyrimidin-4(3H)-one

HRID 591785노트

반응식

HRID 591785 반응식
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[CH:8]=[C:7]([O:15][CH:16]([CH3:18])[CH3:17])[C:3]=1[C:4]([NH2:6])=[O:5].[CH3:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([CH3:36])[C:27]=1[O:28][CH2:29][CH2:30][N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)[CH:23]=O.OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1.Cl>CN(C)C(=O)C.CCOCC>[CH3:36][C:26]1[CH:25]=[C:22]([C:23]2[NH:6][C:4](=[O:5])[C:3]3[C:7]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:8][C:9]([O:11][CH:12]([CH3:13])[CH3:14])=[N:10][C:2]=3[N:1]=2)[CH:21]=[C:20]([CH3:19])[C:27]=1[O:28][CH2:29][CH2:30][N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 23665763Sodium BisulfiteHCID 289325703,5-Dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehydeHCID 666709532-Amino-4,6-diisopropoxy-nicotinamide

생성물 1

HCID 1363480262-(3,5-Dimethyl-4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-5,7-diisopropoxypyrido[2,3-d]pyrimidin-4(3H)-one

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 31374Dimethylacetamide용매

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온도
120 °C

실험 절차

To a solution of 2-amino-4,6-diisopropoxy-nicotinamide (450 mg, 1.78 mmol) and 3,5-dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde (440 mg, 1.78 mmol) in N,N-dimethyl acetamide (10 mL) were added NaHSO3 (790 mg, 4.44 mmol) and p-TSA (845 mg, 4.44 mmol). The reaction mixture was heated at 120° C. for 16 hours, then cooled to room temperature. The solvent was removed under reduced pressure. Then, water (100 mL) was added and stirred for 30 min at room temperature. The separated solids were filtered and dried to give crude product, which was purified by the Simpliflash system, using 2% methanol in dichloromethane, to give a yellow oil, which dissolved in ether. 2N HCl in ether was added, and the separated solids were filtered and dried to give the hydrochloride salt of the title compound as a yellow solid. Yield: 59 mg (6%). 1H NMR (400 MHz, DMSO-d6): δ 10.7 (br s, 1H), 7.88 (s, 2H), 6.31 (s, 1H), 5.41 (m, 1H), 4.80 (m, 1H), 4.14 (t, J=4.8 Hz, 2H), 3.61 (m, 2H), 3.16 (m, 4H), 2.34 (s, 6H), 2.03 (m, 2H), 1.91 (m, 2H), 1.32 (s, 6H), 1.30 (s, 6H). MS (ES) m/z: 481.18 (M+1).

후처리

  1. temperaturecooled to room temperature
  2. customThe solvent was removed under reduced pressure
  3. additionThen, water (100 mL) was added
  4. filtrationThe separated solids were filtered
  5. customdried
  6. customto give crude product, which
  7. customwas purified by the Simpliflash system
  8. customto give a yellow oil, which
  9. filtrationthe separated solids were filtered
  10. customdried

출처 및 근거

ORD 기록
ord-4f9f3e7121ff41bdaffdc70613e5a04a
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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