Triethylamine → Cyclopentyl-{4-[2-methyl-4-(6-pyrrolidin-1-yl-pyrido[3,4-d]pyrimidin-4-ylamino)-phenoxy]-piperidin-1-yl}-methanone

HRID 731908ノート

反応式

HRID 731908 の反応式
[CH:1]1([C:6]([N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]4[C:23]5[CH:31]=[C:30](F)[N:29]=[CH:28][C:24]=5[N:25]=[CH:26][N:27]=4)=[CH:17][C:16]=3[CH3:33])[CH2:10][CH2:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.CCN(CC)CC>CS(C)=O>[CH:1]1([C:6]([N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]4[C:23]5[CH:31]=[C:30]([N:34]6[CH2:38][CH2:37][CH2:36][CH2:35]6)[N:29]=[CH:28][C:24]=5[N:25]=[CH:26][N:27]=4)=[CH:17][C:16]=3[CH3:33])[CH2:10][CH2:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 69051928Cyclopentyl-{4-[4-(6-fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-piperidin-1-yl}-methanone

生成物 1

HCID 11202845Cyclopentyl-{4-[2-methyl-4-(6-pyrrolidin-1-yl-pyrido[3,4-d]pyrimidin-4-ylamino)-phenoxy]-piperidin-1-yl}-methanone収率 40%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution of Cyclopentyl-{4-[4-(6-fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-piperidin-1-yl}-methanone (50 mg, 0.11 mmol), pyrrolodine (15.8 mg, 0.222 mmol), and NEt3 (33.7 mg, 0.333 mmol) in DMSO (1 mL) was heated to 120° C. for 12 h. The reaction was concentrated and purified by preparative HPLC to give the title compound as a yellow solid (22 mg, 40%). MS: 501.4 (MH+); 1H NMR (DMSO-d6, 400 MHz): δ 8.84 (s, 1H), δ 8.30 (s, 1H), δ 7.50-7.54 (m, 2H), δ 7.24 (s, 1H), δ 6.08 (d, J=8.72 Hz, 1H), δ 6.55 (s, 1H), δ 4.52 (m, 1H), δ 3.70 (m, 3H), δ 3.48-3.65 (m, 4H) δ 2.86-2.94 (m, 1H), δ 2.22 (s, 3H), 1.53-2.00 (m, 17H)

後処理

  1. concentrationThe reaction was concentrated
  2. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-52837a6124a24a709eaf5adc45620fb2
出典データセット
uspto-grants-2009_09
特許番号
US07585869B2

反応ノート

読み込み中…