Sodium Carbonate → 4-{8-[3-Chloro-4-(4-methyl-piperazin-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-5-yl}-benzamide

HRID 1366142

반응식

HRID 1366142 반응식
Br[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[C:14]([Cl:25])[CH:13]=2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:34]2[CH:42]=[CH:41][C:37]([C:38]([NH2:40])=[O:39])=[CH:36][CH:35]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C.O1CCOCC1>[Cl:25][C:14]1[CH:13]=[C:12]([NH:11][C:5]2[C:6]3[N:7]([CH:8]=[CH:9][N:10]=3)[C:2]([C:34]3[CH:42]=[CH:41][C:37]([C:38]([NH2:40])=[O:39])=[CH:36][CH:35]=3)=[CH:3][N:4]=2)[CH:17]=[CH:16][C:15]=1[N:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27605884-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 59023078HCID 59023078, 화합물

생성물 1

HCID 590229994-{8-[3-Chloro-4-(4-methyl-piperazin-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-5-yl}-benzamide

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 217120691,4-dioxane N,N-dimethylformamide용매

실험 절차

In the same way as described for Compound 178, step 4, using (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-[3-chloro-4-(4-methyl-piperazin-1-yl)-phenyl]-amine (60.0 mg, 0.14 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (46.0 mg, 0.28 mmol), Pd(PPh3)4 (40.0 mg, 0.035 mmol) and 1.5 M Na2CO3 (0.75 mL, 1.12 mmol) in 2:1 DMF-dioxane (3 mL). The crude residue is triturated with DCM and then the title compound is crystallised from EtOH (4 mg, 6%). LCMS: Rt 2.01 min (96%) m/z (APCI) 462 (M+H)+; 1H-NMR (400 MHz, d6-DMSO) δ (ppm). 2.27 (3H, s), 2.49-2.54 (4H, t), 2.99 (4H, m), 7.19 (1H, d), 7.53 (1H, br s), 7.60 (1H, s), 7.76 (1H, s), 7.84 (2H, d), 7.98 (1H, dd), 8.04 (1H, s), 8.09 (2H, d), 8.13 (1H, br s), 8.35 (1H, s), 9.86 (1H, s).

후처리

  1. customThe crude residue is triturated with DCM
  2. customthe title compound is crystallised from EtOH (4 mg, 6%)

출처 및 근거

ORD 기록
ord-941f76ab1ce345289d56994b75d9d938
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893058B2

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