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Ammonia → 2-(6-((3aR,6aS)-5-(2-hydroxyethyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyridazin-3-yl)-5-(1H-pyrazol-4-yl)phenol

HRID 1027307
Notes
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Reaction equation

HRID 1027307 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH2:15][C@@H:14]2[CH2:16][N:17]([C:19]3[N:24]=[N:23][C:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]5[CH:32]=[N:33][NH:34][CH:35]=5)=[CH:27][C:26]=4[OH:36])=[CH:21][CH:20]=3)[CH2:18][C@@H:13]2[CH2:12]1)(C(C)(C)C)(C)C.Cl.N>O1CCOCC1.CO>[OH:8][CH2:9][CH2:10][N:11]1[CH2:12][C@@H:13]2[CH2:18][N:17]([C:19]3[N:24]=[N:23][C:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]5[CH:35]=[N:34][NH:33][CH:32]=5)=[CH:27][C:26]=4[OH:36])=[CH:21][CH:20]=3)[CH2:16][C@@H:14]2[CH2:15]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 136377186HCID 136377186, compound

Product 1

HCID 1363771872-(6-((3aR,6aS)-5-(2-hydroxyethyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyridazin-3-yl)-5-(1H-pyrazol-4-yl)phenolYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2-(6-((3aR,6aS)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyridazin-3-yl)-5-(1H-pyrazol-4-yl)phenol (20 mg, 0.039 mmol) in dioxane (2 mL) was added 4N HCl in dioxane (1 mL, 4.00 mmol). The reaction mixture was stirred at RT overnight, then basified with 2N NH3 in MeOH and concentrated. The crude product was purified via preparative HPLC to give an off-white solid 2-(6-((3aR,6aS)-5-(2-hydroxyethyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyridazin-3-yl)-5-(1H-pyrazol-4-yl)phenol (6.5 mg, 0.016 mmol, 41% yield). LCMS Rt=0.87 min [Method Q]; MS (M+1)=393.1. 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.01 (d, J=9.60 Hz, 1H), 7.93 (s, 2H), 7.69 (d, J=8.08 Hz, 1H), 7.08-7.19 (m, 3H), 3.67-3.77 (m, 4H), 3.56 (d, J=11.12 Hz, 2H), 3.11 (br. s., 2H), 2.97-3.05 (m, 2H), 2.72 (t, J=5.81 Hz, 2H), 2.63-2.70 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified via preparative HPLC

Sources & evidence

ORD record
ord-4ca9443b79ad41f492ffb3eb3090cb07
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08729263B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes