Hydrochloric Acid → HCID 49855588, compound

HRID 2079813Notes

Reaction equation

HRID 2079813 reaction equation
C(OC([O:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[CH2:23][CH:22]3[CH:20]([CH:21]3[CH2:24][NH:25][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)[CH2:19]2)=[N:16][CH:17]=1)=[O:11])C)C(C)C.Cl.O1CCOCC1>C(Cl)Cl>[OH:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[CH2:23][CH:22]3[CH:20]([CH:21]3[CH2:24][NH:25][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)[CH2:19]2)=[N:16][CH:17]=1)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59367558HCID 59367558, compound

Product 1

HCID 49855588HCID 49855588, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(1-Isobutoxyethoxy) 2-(6-{[(naphthalen-2-ylmethyl)amino]methyl}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxamide (43 mg, 0.09 mmol) was stirred in DCM (2 ml) at r.t. under N2 and 4M HCl in dioxane (45 μl, 0.18 mmol) was added. This immediately caused a solid to precipitate. The reaction was allowed to stir for 10 min and then the solvent was removed in vacuo to give the title compound as a white solid (16 mg, 50%). LCMS purity 98%, m/z 390 [M+H]+, 1H NMR (300 MHz, d6-DMSO) δ: 1.91 (2H, m), 2.50 (1H, m), 2.99 (2H, m), 3.55 (2H, m), 3.88 (2H, d, J=11.7 Hz), 4.34 (2H, m), 7.58 (2H, m), 7.68 (1H, m), 7.95 (2H, m), 8.03 (2H, m), 8.66 (2H, s), 9.11 (2H, br s), 11.07 (1H, br s).

Workup

  1. customto precipitate
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9d21ff11bbce4dd98b5c07f3786c7303
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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