Nicotinic Acid → CID 45138321

HRID 536232ノート

反応式

HRID 536232 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][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.[C:27](O)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[N:30][CH:29]=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.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([NH:13][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[N:30][CH:29]=3)[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][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1

参加物

7

反応物 4

HCID 938Nicotinic AcidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 178493860HCID 178493860、化合物

生成物 1

HCID 178493854CID 45138321収率 42.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

7-Methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (Step 5, 1.0 g, 2.2 mmol) was dissolved in DMF (15 mL), and nicotinic acid (0.44 g, 3.3 mmol) was added. PyBOP (1.73 g, 3.3 mmol) and diisopropylethylamine (1.6 mL, 8.9 mmol) were subsequently added, and the mixture was stirred at rt overnight. EtOAc was added, and the solids were isolated by vacuum filtration to give the title compound (0.43 g, 40%): HPLC MS RT=1.15 min, MH+=463.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 9.01 (2H, s), 8.04 (1H, d), 7.43 (1H, d), 4.54 (2H, m), 4.34 (2H, br t), 4.23 (2H, m), 4.04 (2H, m), 4.00 (3H, s), 3.65 (2H, br t), 3.52 (2H, m), 3.31 (2H, m), 3.18 (2H, m), 2.25 (2H, m).

後処理

  1. customthe solids were isolated by vacuum filtration

出典と根拠

ORDレコード
ord-1bbad070d9a84978b94cfa6baf362bef
出典データセット
uspto-grants-2014_10
特許番号
US08859572B2

反応ノート

読み込み中…