Diisopropylethylamine → HCID 178493823, 화합물

HRID 536245노트

반응식

HRID 536245 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][C:4]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1.[NH2:29][C:30]1[N:35]=[CH:34][C:33]([C:36](O)=[O:37])=[CH:32][N:31]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH2:29][C:30]1[N:35]=[CH:34][C:33]([C:36]([NH:13][C:10]2[N:9]3[CH2:14][CH2:15][N:16]=[C:8]3[C:7]3[CH:6]=[CH:5][C:4]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=4)=[C:3]([O:2][CH3:1])[C:12]=3[N:11]=2)=[O:37])=[CH:32][N:31]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 70203672-aminopyrimidine-5-carboxylic AcidHCID 178493824HCID 178493824, 화합물

생성물 1

HCID 178493823HCID 178493823, 화합물수율 12.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

7-Methoxy-8-{[4-(methylsulfonyl)benzyl]oxy}-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (Step 1, 76 mg, 0.19 mmol) was dissolved in DMF (5 mL), and 2-aminopyrimidine-5-carboxylic acid (40 mg, 0.29 mmol) was added. PyBOP (152 mg, 0.29 mmol) and diisopropylethylamine (0.15 mL, 0.85 mmol) were subsequently added. The mixture was stirred at it overnight, during which a tan solid precipitated. The DMF was removed under reduced pressure and the residue purified via silica gel chromatography (0-3% MeOH/CH2Cl2+0.1% Et3N). The solvent was evaporated under reduced pressure, the residue triturated in water (5 mL), collected by vacuum filtration, then washed with acetone. High vacuum drying gave the title compound (12 mg, 12%): HPLC MS RT=2.06 min, MH+=522.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 3.22 (3H, s), 4.00 (3H, s), 4.19-4.25 (2H, m), 4.48-4.55 (2H, m), 5.53 (2H, s), 7.53 (1H, d), 7.77 (2H, d), 7.97-8.03 (3H, m), 9.06 (2H, s).

후처리

  1. customprecipitated
  2. customThe DMF was removed under reduced pressure
  3. customthe residue purified via silica gel chromatography (0-3% MeOH/CH2Cl2+0.1% Et3N)
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue triturated in water (5 mL)
  6. filtrationcollected by vacuum filtration
  7. washwashed with acetone
  8. customHigh vacuum drying

출처 및 근거

ORD 기록
ord-4511cf258c8f412eb912933c7e37f00a
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859572B2

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