Hydrochloric Acid → 7-(3-pyrrolidin-2-yl-benzoylamino)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester HCl

HRID 1524295Notes

Reaction equation

HRID 1524295 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([NH:21][C:22](=[O:41])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]4[CH2:33][CH2:32][CH2:31][N:30]4C(OC(C)(C)C)=O)[CH:24]=3)=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:42].O1CCOCC1>C(Cl)Cl>[ClH:42].[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([NH:21][C:22](=[O:41])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]4[CH2:33][CH2:32][CH2:31][NH:30]4)[CH:24]=3)=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 666551417-[3-(1-tert-butoxycarbonyl-pyrrolidin-2-yl)-benzoylamino]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

Product 1

HCID 666549657-(3-pyrrolidin-2-yl-benzoylamino)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester HCl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-[3-(1-tert-butoxycarbonyl-pyrrolidin-2-yl)-benzoylamino]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (900 mg, 1.62 mmol) in methylene chloride (50 mL) add 4M HCl in dioxane (8.1 mL, (32.4 mmol)) and stir the reaction at room temperature for 24 h. Remove the solvents in vacuo at 40° C., dissolve the residue in EtOAc, and concentrate again concentrate to dryness. Dry the residue in vacuo then triturate in EtOAc and hexane to afford 2.63 g of 7-(3-pyrrolidin-2-yl-benzoylamino)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester HCl as a solid.

Workup

  1. customthe reaction at room temperature for 24 h
  2. customRemove the solvents in vacuo at 40° C.
  3. dissolutiondissolve the residue in EtOAc
  4. concentrationconcentrate again
  5. concentrationconcentrate to dryness
  6. customDry the residue in vacuo
  7. customthen triturate in EtOAc

Sources & evidence

ORD record
ord-b11f4a532fb54362ba0b126b741d2273
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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