Potassium Phosphate, Tribasic → 6-(4-(Aminomethyl)phenyl)-1-(cyclohexylmethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 1014699ノート

反応式

HRID 1014699 の反応式
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([C:17]4[CH:31]=[CH:30][C:20]([CH2:21][NH:22]C(=O)OC(C)(C)C)=[CH:19][CH:18]=4)[N:15]=3)[NH:10][C:9]2=[O:32])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.BrC1N=C2N(CC3CCCCC3)C(=O)NC2=NC=1.C(NCC1C=CC(B(O)O)=CC=1)(OC(C)(C)C)=O.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]>[NH2:22][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([C:14]2[N:15]=[C:16]3[N:8]([CH2:7][CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[C:9](=[O:32])[NH:10][C:11]3=[N:12][CH:13]=2)=[CH:31][CH:30]=1

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 38631634-(tert-Butoxycarbonylaminomethyl)phenylboronic acidHCID 866263916-Bromo-1-(cyclohexylmethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-oneHCID 86626393tert-Butyl 4-(3-(cyclohexylmethyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)benzylcarbamate

生成物 1

HCID 573943616-(4-(Aminomethyl)phenyl)-1-(cyclohexylmethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

試薬・触媒・溶媒 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

tert-Butyl 4-(3-(cyclohexylmethyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)benzylcarbamate. 6-Bromo-1-(cyclohexylmethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (See Example 55.B) (200 mg, 0.64 mmol), [4-(N-boc-aminomethyl)phenyl]boronic acid (195 mg, 0.77 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane (53 mg, 0.06 mmol) and potassium phosphate (550 mg, 2.58 mmol) in DMF (15 mL) and water (1 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 to approximately one third the original volume and treated with potassium carbonate (1.75 M). The desired product was collected by vacuum filtration, washed with water and dried under high vacuum to provide the title compound. The product was used directly in the next step without further purification or characterization. MS (ESI) m/z 438.1 [M+1]+.

後処理

  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 to approximately one third the original volume
  3. additiontreated with potassium carbonate (1.75 M)
  4. filtrationThe desired product was collected by vacuum filtration
  5. washwashed with water
  6. customdried under high vacuum

出典と根拠

ORDレコード
ord-f8aa2528d1d94300b219d9f4e78fd95e
出典データセット
uspto-grants-2011_07
特許番号
US07981893B2

反応ノート

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