Cesium carbonate → HCID 69265746, compound

HRID 1352768Notes

Reaction equation

HRID 1352768 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([Cl:28])[CH:21]=2)[C:5]([C:8]([NH:10][CH2:11][C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:9])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:81]1[CH2:87][CH2:86][CH2:85][C@H:82]1[CH2:83][OH:84].C(=O)([O-])O.[Na+]>COCCOCCOC>[Cl:28][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[O:26][CH3:27])[CH2:19][NH:18][C:4]1[C:5]([C:8]([NH:10][CH2:11][C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:9])=[N:6][CH:7]=[C:2]([N:81]2[CH2:87][CH2:86][CH2:85][C@H:82]2[CH2:83][OH:84])[CH:3]=1

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 634876Binap, (A+-)-HCID 640091L-ProlinolHCID 17848362HCID 17848362, compound

Product 1

HCID 69265746HCID 69265746, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
120 °C

Procedure

In diglyme 2 ml are suspended 5-bromo-3-(3-chloro-4-methoxybenzylamino)-2-(2-pyrimidinylmethylaminocarbonyl)pyridine (prepared in the above (5)) 20 mg, trisdibenzylidene acetone palladium (0) 22 mg, 2,2′-bisdiphenylphosphino-1,1′-binaphthyl 4 mg, cesium carbonate 43 mg and L-prolinol 88 mg, and the mixture is stirred at 120° C. for 5 hours. An aqueous saturated sodium hydrogen carbonate solution is added to the reaction mixture cooled, and the mixture is extracted with ethyl acetate. The combined organic layer is washed, dried and the solvent is removed in vacuo. The residue is purified by silica gel preparative thin-layer chromatography (developing solution; ethyl acetate) to give (S)-(3-chloro-4-methoxybenzylamino)-5-(2-hydroxymethyl-1-pyrrolidinyl)-2-(2-pyrimidinylmethylaminocarbonyl)pyridine as a pale brown powder 5.2 mg. MS(m/z): 483(M+H)+

Workup

  1. temperaturecooled
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe combined organic layer is washed
  4. customdried
  5. customthe solvent is removed in vacuo
  6. customThe residue is purified by silica gel preparative thin-layer chromatography (developing solution; ethyl acetate)

Sources & evidence

ORD record
ord-e79274500f0340228ff98783a4d94e19
Source dataset
uspto-grants-2007_05
Patent number
US07220736B2

Reaction notes

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