4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide → 4-[8-(4-Methanesulfonyl-phenylamino)-imidazo[1,2-a]pyrazin-5-yl]-benzamide

HRID 1366122

반응식

HRID 1366122 반응식
N1(C2C=CC(NC3C4N(C=CN=4)C(C4C=CNC(=O)C=4)=CN=3)=CC=2)CCOCC1.CC1(C)C(C)(C)OB([C:38]2[CH:46]=[CH:45][C:41]([C:42]([NH2:44])=[O:43])=[CH:40][CH:39]=2)O1.Br[C:49]1[N:54]2[CH:55]=[CH:56][N:57]=[C:53]2[C:52]([NH:58][C:59]2[CH:64]=[CH:63][C:62]([S:65]([CH3:68])(=[O:67])=[O:66])=[CH:61][CH:60]=2)=[N:51][CH:50]=1.CC([O-])(C)C.[Na+]>CN(C=O)C.O.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>[CH3:68][S:65]([C:62]1[CH:63]=[CH:64][C:59]([NH:58][C:52]2[C:53]3[N:54]([CH:55]=[CH:56][N:57]=3)[C:49]([C:38]3[CH:39]=[CH:40][C:41]([C:42]([NH2:44])=[O:43])=[CH:45][CH:46]=3)=[CH:50][N:51]=2)=[CH:60][CH:61]=1)(=[O:66])=[O:67]

참가 물질

8

반응물 4

HCID 27605884-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 23676156Sodium t-butoxideHCID 248574474-[8-(4-Morpholin-4-yl-phenylamino)imidazo[1,2-a]pyrazin-5-yl]-1H-pyridin-2-oneHCID 59022984(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(4-methanesulfonyl-phenyl)-amine

생성물 1

HCID 248576534-[8-(4-Methanesulfonyl-phenylamino)-imidazo[1,2-a]pyrazin-5-yl]-benzamide

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

In the same way as described for Compound 85, step 1, using 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (1.0 g, 6.11 mmol), (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-(4-methanesulfonyl-phenyl)-amine (1.49 g, 4.07 mmol), Pd(PPh3)4 (471 mg, 0.41 mmol) and NaOtBu (1.57 g, 0.82 mmol) in DMF (18 mL) and water (6 mL). The residue is chromatographed on silica gel, eluting with DCM followed by 95:5 DCM:NH3 (7M in MeOH), and the fractions containing the desired product are combined and evaporated to afford a solid, crystallised in ethyl acetate (566 mg, 34%). LCMS: Rt 2.53 min (99%), m/z (APCI) 408 (M+H)+; 1H-NMR (400 MHz, d6-DMSO δ(ppm) 3.21 (3H, s), 7.54 (1H, br s), 7.67 (1H, s), 7.81 (1H, s), 7.86-7.92 (4H, m), 8.09-8.17 (3H, m), 8.21 (1H, br s), 8.41 (2H, d), 10.32 (1H, s).

후처리

  1. customThe residue is chromatographed on silica gel
  2. washeluting with DCM
  3. additionNH3 (7M in MeOH), and the fractions containing the desired product
  4. customevaporated
  5. customto afford a solid
  6. customcrystallised in ethyl acetate (566 mg, 34%)

출처 및 근거

ORD 기록
ord-851af5bc762143cd9f6b29238e7a6800
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893058B2

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