4-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one → 4-(3-Chloro-4-fluoro-phenylamino)-5-[5-(3,5-dimethyl-piperazine-1-carbonyl)-3-methyl-1H-pyrrol-2-ylmethylene]-5,7-dihydro-pyrrolo[2,3-D]pyrimidin-6-one

HRID 1072194ノート

反応式

HRID 1072194 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH2:18][C:17](=[O:19])[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:20][CH:21]1[NH:26][CH:25]([CH3:27])[CH2:24][N:23]([C:28]([C:30]2[NH:34][C:33]([CH:35]=O)=[C:32]([CH3:37])[CH:31]=2)=[O:29])[CH2:22]1>N1CCCCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18](=[CH:35][C:33]4[NH:34][C:30]([C:28]([N:23]5[CH2:22][CH:21]([CH3:20])[NH:26][CH:25]([CH3:27])[CH2:24]5)=[O:29])=[CH:31][C:32]=4[CH3:37])[C:17](=[O:19])[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

参加物

5

反応物 2

HCID 98787694-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-oneHCID 22391003HCID 22391003、化合物

生成物 1

HCID 697986994-(3-Chloro-4-fluoro-phenylamino)-5-[5-(3,5-dimethyl-piperazine-1-carbonyl)-3-methyl-1H-pyrrol-2-ylmethylene]-5,7-dihydro-pyrrolo[2,3-D]pyrimidin-6-one収率 73%

試薬・触媒・溶媒 2

HCID 8082Piperidine触媒HCID 702Ethanol溶媒

実験手順

A mixture of 4-(3-chloro-4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (70 mg, 0.25 mmol), 5-(3,5-dimethyl-piperazine-1-carbonyl)-3-methyl-1H-pyrrole-2-carbaldehyde (74.8 mg, 0.3 mmol) and piperidine (3 drops) in ethanol (2 mL) was stirred at room temperature for overnight. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 93.1 mg (73%) of the title compound as a yellow solid. 1H NMR (360 MHz, DMSO-d6) δ 13.39 (br s, 1H, NH), 11.75 (br s, 1H, NH), 9.23 (br s, 1H), 8.32 (s, 1H), 7.73 (dd, J=2.6 & 6.7 Hz, 1H), 7.41 (m, 1H), 7.33-7.38 (m, 2H), 6.57 (d, J=2 Hz, 1H), 4.22 (m, 2H, CH2), 2.68 (m, 2H, CH2), 2.52 (m, 2H, 2×CH), 2.22 (s, 3H, CH3), 0.99 (d, J=6 Hz, 6H, 2×CH3), 0.98 (s, 3H, CH3). MS 510 [M++1].

後処理

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with ethanol
  3. customdried

出典と根拠

ORDレコード
ord-1c10b3ab4e424a07b2129a3cf4bf9bcc
出典データセット
uspto-grants-2005_06
特許番号
US06908930B2

反応ノート

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