Hydrochloric Acid → Hydrochloric Acid

HRID 1628067Notes

Reaction equation

HRID 1628067 reaction equation
[OH:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([C@@H:33]3[CH2:37][CH2:36][C@H:35]([NH:38]C(=O)OC(C)(C)C)[CH2:34]3)[N:14]3[C:19]4[CH:20]=[CH:21][N:22]([S:23]([C:26]5[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=5)(=[O:25])=[O:24])[C:18]=4[N:17]=[CH:16][C:15]=23)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].O1CCOCC1.[ClH:52]>CCOCC>[NH2:38][C@H:35]1[CH2:36][CH2:37][C@@H:33]([C:13]2[N:14]3[C:19]4[CH:20]=[CH:21][N:22]([S:23]([C:26]5[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=5)(=[O:24])=[O:25])[C:18]=4[N:17]=[CH:16][C:15]3=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([C:2]([OH:1])([CH3:3])[CH3:4])=[CH:10][CH:9]=3)[N:12]=2)[CH2:34]1.[ClH:52]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68266069HCID 68266069, compound

Product 2

HCID 313Hydrochloric AcidYield 1,407.4%HCID 58382358HCID 58382358, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

To a flask was added tert-butyl (1S,3R)-3-(3-(4-(2-hydroxypropan-2-yl)phenyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)cyclopentylcarbamate (0.48 g, 0.76 mmol; prepared using J.1 from Example #2, Step B with (1R,3S)-3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid [PepTech], L.1 with mercury(II) trifluoroacetate, AB and D with Preparation #H.1), 1,4-dioxane (7.6 mL) and HCl (4.0 M in 1,4-dioxane, 1.9 mL, 7.6 mmol). The reaction mixture was heated to about 60° C. for about 30 min. The mixture was cooled to rt and diluted with Et2O (20 mL). The solid was collected by filtration, washed with Et2O (10 mL) and dried under reduced pressure at about 60° C. overnight to give 2-(4-(1-((1R,3S)-3-aminocyclopentyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol, hydrochloric acid (0.39 g, 91% yield): LC/MS (Table 2, Method a) Rt=3.06 min; MS m/z 574 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationThe solid was collected by filtration
  3. washwashed with Et2O (10 mL)
  4. customdried under reduced pressure at about 60° C. overnight

Sources & evidence

ORD record
ord-8a1a2dfa8a0d47518149d30e3e0b04bc
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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