Hydrochloric Acid → HCID 67116468, compound

HRID 244010Notes

Reaction equation

HRID 244010 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:13][CH:12]3[CH2:14][N:15]([C:17]([C:19]4[C:20]([C:25]5[N:29](C6CCCCO6)[N:28]=[CH:27][CH:26]=5)=[N:21][CH:22]=[CH:23][CH:24]=4)=[O:18])[CH2:16][CH:11]3[CH2:10]2)[N:3]=1.Cl.[OH-].[Na+]>C1COCC1.O>[NH:29]1[C:25]([C:20]2[C:19]([C:17]([N:15]3[CH2:16][CH:11]4[CH:12]([CH2:13][N:9]([C:4]5[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=5)[CH2:10]4)[CH2:14]3)=[O:18])=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:26][CH:27]=[N:28]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67116153HCID 67116153, compound

Product 1

HCID 67116468HCID 67116468, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-(4,6-dimethylpyrimidin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)pyridin-3-yl)methanone (Example 236) (210 mg, 0.43 mmol) in THF (10 mL) and H2O (1 mL) was added 4 N aq. HCl (1 mL). The reaction was let stir for 2 hours, neutralized with 3 N aq. NaOH, and extracted with DCM (3×20 mL). The organics were combined, dried with Na2SO4, and concentrated. Purification (FCC) (MeOH(NH3)/DCM) gave the title compound (128 mg, 73%) (MS (ESI): mass calculated for C21H23N7O, 389.20; m/z found 390.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.68-8.59 (m, 1H), 7.63 (d, J=9.1, 2H), 7.32-7.20 (m, 1H), 6.80 (d, J=2.2, 1H), 6.33-6.19 (m, 1H), 3.92-3.55 (m, 5H), 3.54-2.78 (m, 5H), 2.37-2.24 (m, 6H).

Workup

  1. extractionextracted with DCM (3×20 mL)
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated
  4. customPurification (FCC) (MeOH(NH3)/DCM)

Sources & evidence

ORD record
ord-ee7ba3ae3bcf4d21b2bbb99490d45354
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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