Hydrochloric Acid → HCID 131723696, compound

HRID 2298096Notes

Reaction equation

HRID 2298096 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[CH:25]12[CH2:31][CH:28]([NH:29][CH2:30]1)[CH2:27][N:26]2C(OC(C)(C)C)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>CO.O1CCOCC1.ClCCCl>[ClH:1].[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][N:26]2[CH2:27][CH:28]3[CH2:31][CH:25]2[CH2:30][NH:29]3)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]3)[CH2:15]1)[CH2:9]2)=[O:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 2760898(1S,4S)-tert-butyl 2,5-diazabicyclo(2.2.1)heptane-2-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 18381537HCID 18381537, compound

Product 1

HCID 131723696HCID 131723696, compoundYield 106.2%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Prepared according to the method described in Example 66c from 2-chloro-5-(2-oxoethyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.094 g, Example 66b), 2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid, 1,1-dimethylethyl ester (0.108 g), sodium triacetoxyborohydride (0.081 g) and 1,2-dichloroethane (2 ml). After work-up, the residue was purified by HPLC eluting with a gradient of 0-5% ethanol in dichloromethane. The white powder obtained was dissolved in methanol (2 ml) and a solution of hydrochloric acid in dioxane (4N, 1 ml) was added. The mixture was stirred for 14 h at room temperature. Solvents were then removed under reduced pressure and the product obtained was triturated with diethyl ether to afford the title compound as a white powder (0.067 g).

Workup

  1. customPrepared
  2. customAfter work-up, the residue was purified by HPLC
  3. washeluting with a gradient of 0-5% ethanol in dichloromethane
  4. customThe white powder obtained
  5. customSolvents were then removed under reduced pressure
  6. customthe product obtained
  7. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-8d516846fefe4d2f85eb9b14cf2e6c30
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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