Nicotinic Acid → HCID 178488374, 화합물

HRID 536222노트

반응식

HRID 536222 반응식
[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([NH2:13])[N:9]3[CH2:14][CH2:15][N:16]=[C:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1.[C:17](O)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=1.C(N(C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([NH:13][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=3)[N:9]3[CH2:14][CH2:15][N:16]=[C:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 938Nicotinic AcidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 178488375HCID 178488375, 화합물

생성물 1

HCID 178488374HCID 178488374, 화합물수율 68%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

7-Methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (Step 4, 31.2 g, 57.7 mmol), nicotinic acid (10.7 g, 86 mmol) and diisopropylethylamine (30.1 mL, 173 mmol) were suspended in DMF (250 mL), and PyBOP (45 g, 86 mmol) was added portionwise. The reaction soon became much thicker with a new solid. After stirring overnight, the solid was collected by filtration then washed with EtOAc (150 mL). The solid was dissolved in CH2Cl2 (1000 mL), washed with water (600 mL) and the organic layer dried over Na2SO4. The solvent was removed under reduced pressure to give the title compound (12.6 g, 68%): HPLC MS RT=1.18 min, MH+=322.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 4.12 (3H, s), 4.28-4.35 (2H, m), 4.60-4.66 (2H, m), 7.63 (1H, t), 7.72-7.86 (3H, m), 8.76 (1H, d), 8.93 (1H, dd), 9.48 (1H, d).

후처리

  1. customThe reaction
  2. filtrationthe solid was collected by filtration
  3. washthen washed with EtOAc (150 mL)
  4. dissolutionThe solid was dissolved in CH2Cl2 (1000 mL)
  5. washwashed with water (600 mL)
  6. dry with materialthe organic layer dried over Na2SO4
  7. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-9d2e9468f0a645dba17f4ee7c327e0b6
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859572B2

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