Potassium Phosphate, Tribasic → HCID 24983905, 화합물

HRID 1014700

반응식

HRID 1014700 반응식
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26]C)=[O:25])=[CH:19][CH:18]=4)[N:15]=3)[NH:10][C:9]2=[O:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC1(C)C(C)(C)OB(C2C=CC(CC(OC)=O)=CC=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.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]>[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([C:17]4[CH:18]=[CH:19][C:20]([CH2:23][C:24]([OH:26])=[O:25])=[CH:21][CH:22]=4)[N:15]=3)[NH:10][C:9]2=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 11219601Methyl 2-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetateHCID 66699783HCID 66699783, 화합물

생성물 1

HCID 24983905HCID 24983905, 화합물

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

Methyl 2-(4-(3-(cyclohexylmethyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)phenyl)acetate. Bromo-1-(cyclohexylmethyl)-4-imidazolino[4,5-b]pyrazin-2-one (200 mg, 0.64 mmol), methyl 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate (213 mg, 0.77 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane (53 mg, 0.06 mmol) and potassium phosphate (543 mg, 2.56 mmol) in DMF (20 mL) and water (5 mL) were reacted according to General Procedure B. The product was purified by reverse-phase semi-preparatory HPLC (30-100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). The desired fractions were concentrated, and the residue was taken up in DMSO (2 mL) and heated at 100° C. until completely dissolved. Water was added upon cooling and the desired product precipitated out of solution. The precipitate was collected by vacuum filtration, washed with water and dried under high vacuum to provide the title compound (95 mg, 39 yield) as a tan solid. MS (ESI) m/z 381.4 [M+1]+.

후처리

  1. customThe product was purified by reverse-phase semi-preparatory HPLC (30-100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min)
  2. concentrationThe desired fractions were concentrated
  3. dissolutionuntil completely dissolved
  4. additionWater was added
  5. temperatureupon cooling
  6. customthe desired product precipitated out of solution
  7. filtrationThe precipitate was collected by vacuum filtration
  8. washwashed with water
  9. customdried under high vacuum

출처 및 근거

ORD 기록
ord-173cc5138b574c71b156a30d32726433
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981893B2

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