Cesium carbonate → HCID 131723686, compound

HRID 2298078Notes

Reaction equation

HRID 2298078 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][CH2:9][C:10]23[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]4)[CH2:11]2)[CH2:17]3)=[O:7])=[C:4]([Cl:22])[CH:3]=1.[NH2:23][CH:24]1[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[ClH:22].[Cl:22][C:4]1[CH:3]=[C:2]([NH:23][CH:24]2[CH2:28][CH2:27][NH:26][CH2:25]2)[CH:21]=[CH:20][C:5]=1[C:6]([NH:8][CH2:9][C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2)=[O:7]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 27563701-Boc-3-aminopyrrolidineHCID 18381539HCID 18381539, compound

Product 1

HCID 131723686HCID 131723686, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to the method described in Example 41b from 4-bromo-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.25 g, Example 41a), 3-amino-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester (0.182 g, Journal of Medicinal Chemistry, 1998, 41 (22), 4273-4278), cesium carbonate (0.347 g), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.036 g), palladium (II) acetate (0.009 g) and anhydrous toluene (3 ml). The residue was purified by HPLC eluting with a gradient of 0-5% ethanol in dichloromethane. The product was dissolved in methanol and stirred at room temperature for 3 h in the presence of 4N hydrochloric acid solution in dioxane (2 ml). The solution was concentrated under reduced pressure and triturated with diethyl ether to give the title compound as a white powder (0.057 g).

Workup

  1. customPrepared
  2. customThe residue was purified by HPLC
  3. washeluting with a gradient of 0-5% ethanol in dichloromethane
  4. dissolutionThe product was dissolved in methanol
  5. concentrationThe solution was concentrated under reduced pressure
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-16078d7e74984b278ae3a393e83aae6d
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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