Hydrochloric Acid → 1-[6-(4-Fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2R,5R)-5-methyl-2-((R)-3-methyl-morpholin-4-ylmethyl)-piperazin-1-yl]-ethanone hydrochloride

HRID 1475531Notes

Reaction equation

HRID 1475531 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][C:7]2[CH:8]=[C:9]3[N:15]([C:16](=[O:33])[CH2:17][N:18]4[CH2:23][C@@H:22]([CH3:24])[NH:21][CH2:20][C@@H:19]4[CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][C@H:27]4[CH3:32])[CH2:14][C:13]([CH3:35])([CH3:34])[C:10]3=[N:11][CH:12]=2)=[CH:4][CH:3]=1.[ClH:38]>CCOC(C)=O.O1CCOCC1.C(O)(C)C>[ClH:38].[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][C:7]2[CH:8]=[C:9]3[N:15]([C:16](=[O:33])[CH2:17][N:18]4[CH2:23][C@@H:22]([CH3:24])[NH:21][CH2:20][C@@H:19]4[CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][C@H:27]4[CH3:32])[CH2:14][C:13]([CH3:35])([CH3:34])[C:10]3=[N:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 70980530AT-Iap

Product 1

HCID 867240461-[6-(4-Fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2R,5R)-5-methyl-2-((R)-3-methyl-morpholin-4-ylmethyl)-piperazin-1-yl]-ethanone hydrochloride

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

1-[6-(4-Fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2R,5R)-5-methyl-2-((R)-3-methyl-morpholin-4-ylmethyl)-piperazin-1-yl]-ethanone (1.72 g) was dissolved in EtOAc (40 mL) then treated dropwise with a mixture of 4 M HCl in dioxane and EtOAc (40 mL) while stirring at ambient temperature. The resulting clear solution was allowed to stand for 64 h then was evaporated in vacuo to give a foam which was dissolved in isopropanol then re-evaporated. The resulting residue was triturated with ether to afford the title compound (1.43 g) as a white powder. 1H NMR (Me-d3-OD): 8.19 (1H, s), 8.13 (1H, s), 7.31-7.19 (2H, m), 7.04 (2H, t), 4.16-3.79 (7H, m), 3.79-3.42 (4H, m), 3.02 (5H, m), 2.61-1.92 (2H, m), 1.42 (6H, d), 1.32 (3H, s), 1.17 (3H, d), 1.16-0.77 (3H, m).

Workup

  1. customthen was evaporated in vacuo
  2. customto give a foam which
  3. customthen re-evaporated
  4. customThe resulting residue was triturated with ether

Sources & evidence

ORD record
ord-9151df9c83354cc6b6ea8ac934d2c322
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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