Hydrochloric Acid → HCID 53251954, compound

HRID 2092741Notes

Reaction equation

HRID 2092741 reaction equation
N1CCCC(NC(=O)OC(C)(C)C)C1.[O:15]=[C:16]1[C:24]2[C:23]([NH:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)=[N:22][C:21]([N:33]3[CH2:38][CH2:37][CH2:36][CH:35]([NH:39]C(=O)OC(C)(C)C)[CH2:34]3)=[N:20][C:19]=2[CH2:18][NH:17]1.Cl.O1CCOCC1.[OH-].[Na+]>>[NH2:39][CH:35]1[CH2:36][CH2:37][CH2:38][N:33]([C:21]2[N:22]=[C:23]([NH:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[C:24]3[C:16](=[O:15])[NH:17][CH2:18][C:19]=3[N:20]=2)[CH2:34]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 42330413-(Boc-amino)piperidineHCID 67239554HCID 67239554, compound

Product 1

HCID 53251954HCID 53251954, compoundYield 64.8%

Procedure

The above compound was prepared in a manner similar to EXAMPLE 10 using tert-butyl piperidin-3-ylcarbamate in place of cyclohexylamine. Following cyclization, tert-butyl 1-(5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)piperidin-3-ylcarbamate (20.00 mg, 0.046 mmol) was treated with 4M HCl in dioxane (2 mL, 8.00 mmol) at RT for 5 h to deprotect the Boc group. The mixture was subsequently basified with 2N NaOH, extracted with EtOAc, washed with brine, dried over MgSO4, and evaporated. The residue was purified by recrystallization (EtOH-Hexane) to give the title compound as white solid (10 mg, 64.8% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.99-2.03 (m, 4H), 2.30 (s, 3H), 2.57-3.07 (m, 3H), 4.16 (s, 2H), 4.26-4.86 (m, 2H), 6.88 (d, J=5.6 Hz, 1H), 7.23 (s, 1H), 7.42-7.55 (m, 1H), 7.59 (s, 1H), 8.08 (s, 1H), 8.55 (s, 1H). [M+H] calc'd for C18H22N6O, 339. found, 339.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was purified by recrystallization (EtOH-Hexane)

Sources & evidence

ORD record
ord-2664a6cb6d4248c4be5dc4ec08bbb59e
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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