Diisopropylethylamine → HCID 178493823、化合物

HRID 536245ノート

反応式

HRID 536245 の反応式
[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

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 70203672-aminopyrimidine-5-carboxylic AcidHCID 178493824HCID 178493824、化合物

生成物 1

HCID 178493823HCID 178493823、化合物収率 12.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4511cf258c8f412eb912933c7e37f00a
出典データセット
uspto-grants-2014_10
特許番号
US08859572B2

反応ノート

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