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

HRID 1184836노트

반응식

HRID 1184836 반응식
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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-684405cc8ee8420ab4c6d5ac3436ab8e
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669256B2

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