Potassium Carbonate → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-methylthieno[2,3-b]pyrazine-6-carboxamide

HRID 1184836ノート

反応式

HRID 1184836 の反応式
Cl[C:2]1[N:3]=[C:4]2[CH:10]=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([NH:20][C:21](=[O:33])[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([C:31]#[N:32])([CH3:30])[CH3:29])[CH:23]=4)[CH:17]=[CH:16][C:15]=3[CH3:34])=[O:12])[S:8][C:5]2=[N:6][CH:7]=1.[C:35](=O)([O-])[O-].[K+].[K+]>C1COCC1.[NH4+].[Cl-].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:31]([C:28]([C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[C:21]([NH:20][C:18]1[CH:17]=[CH:16][C:15]([CH3:34])=[C:14]([NH:13][C:11]([C:9]2[S:8][C:5]3=[N:6][CH:7]=[C:2]([CH3:35])[N:3]=[C:4]3[CH:10]=2)=[O:12])[CH:19]=1)=[O:33])([CH3:30])[CH3:29])#[N:32]

参加物

6

反応物 2

HCID 11430Potassium CarbonateHCID 547564232-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide

生成物 1

HCID 67125588N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-methylthieno[2,3-b]pyrazine-6-carboxamide収率 13%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

実験手順

A solution of 2-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 24 (40 mg, 0.082 mmol), potassium carbonate (22.56 mg, 0.163 mmol) and 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II) (5.91 mg, 8.16 μmol) in THF was heated to 60° C. for 6 h. The reaction mixture was poured in NH4Cl solution and extracted twice with EtOAc. Organic layer was washed with water, brine, dried and evaporated. Crude product triturated twice with CH2Cl2 to give N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-methylthieno[2,3-b]pyrazine-6-carboxamide 251 (5 mg, 13%). NMR (400 MHz, DMSO-d6) 1.75 (s, 6H), 2.26 (s, 3H), 2.68 (s, 3H), 7.31 (d, J=8.2 Hz, 1H), 7.60 (t, J=7.8 Hz, 1H), 7.66 (d, J=8.6 Hz, 1H), 7.75 (m, 1H), 7.87 (d, J=2.3 Hz, 1H), 7.96 (d, J=7.4 Hz, 1H), 8.06 (s, 1H), 8.47 (s, 1H), 8.67 (s, 1H), 10.40 (s, 1H), 10.54 (br s, 1H). (m/z)=470 (M+H)+.

後処理

  1. extractionextracted twice with EtOAc
  2. washOrganic layer was washed with water, brine
  3. customdried
  4. customevaporated
  5. customCrude product triturated twice with CH2Cl2

出典と根拠

ORDレコード
ord-684405cc8ee8420ab4c6d5ac3436ab8e
出典データセット
uspto-grants-2014_03
特許番号
US08669256B2

反応ノート

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