Hydrochloric Acid → HCID 131721346, compound

HRID 1739115Notes

Reaction equation

HRID 1739115 reaction equation
CC([O-:5])(C)C.[K+].[OH2:7].[ClH:8].[Cl:9][C:10]1[CH:11]=[C:12]([CH:17]([CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][C:34]([CH2:43][O:44][C:45](NCC)=[O:46])([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:33][CH2:32]2)[CH2:18][N:19]([CH3:28])[C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:13]=[CH:14][C:15]=1[Cl:16].O.O.[Cl:52][C:53]1[CH:54]=[C:55]([CH:60]([CH2:72][CH2:73][N:74]2[CH2:79][CH2:78][C:77]([C:87]3[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=3)([CH2:80][O:81][C:82](NCC)=[O:83])[CH2:76][CH2:75]2)[CH2:61][N:62]([CH3:71])[C:63](=[O:70])[C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[CH:56]=[CH:57][C:58]=1[Cl:59].Cl.Cl>CN(C=O)C>[OH2:5].[ClH:9].[C:45]([CH2:80][C:77]1([C:87]2[CH:88]=[CH:89][CH:90]=[CH:91][CH:92]=2)[CH2:78][CH2:79][N:74]([CH2:73][CH2:72][CH:60]([C:55]2[CH:56]=[CH:57][C:58]([Cl:59])=[C:53]([Cl:52])[CH:54]=2)[CH2:61][N:62]([CH3:71])[C:63](=[O:70])[C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[CH2:75][CH2:76]1)([OH:46])=[O:44].[OH2:27].[OH2:7].[C:82]([CH2:43][C:34]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:33][CH2:32][N:31]([CH2:30][CH2:29][CH:17]([C:12]2[CH:13]=[CH:14][C:15]([Cl:16])=[C:10]([Cl:9])[CH:11]=2)[CH2:18][N:19]([CH3:28])[C:20](=[O:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:36][CH2:35]1)([OH:83])=[O:81].[ClH:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 131721345HCID 131721345, compound

Product 1

HCID 131721346HCID 131721346, compoundYield 136.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1.8 g of potassium tert-butylate and then 1.5 g of the compound obtained in step C of EXAMPLE 15 are added to a solution of 2.3 g of the compound obtained in PREPARATION 1.22 in 20 ml of DMF, and the reaction mixture is heated to 80° C. for 2 hours. It is concentrated under vacuum, the residue is taken up in water, the mixture is neutralized to pH 7 by adding concentrated HCl solution, the product is extracted with DCM, the organic phase is washed with water and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H, eluting with a DCM/MeOH (95:5; v/v) mixture. The product obtained is taken up with ethereal hydrogen chloride and the solvent is evaporated off under vacuum. 0.96 g of the expected product is obtained after crystallization in iso ether.

Workup

  1. concentrationIt is concentrated under vacuum
  2. additionby adding concentrated HCl solution
  3. extractionthe product is extracted with DCM
  4. washthe organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica H
  8. washeluting with a DCM/MeOH (95:5; v/v) mixture
  9. customThe product obtained
  10. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-eefc5adeaa75402a95270b7b6ead6ac5
Source dataset
uspto-grants-1999_10
Patent number
US05965580

Reaction notes

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