Hydrochloric Acid → HCID 59367590, compound

HRID 2079796Notes

Reaction equation

HRID 2079796 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[N:24]([C:36](=[O:44])[CH2:37][CH2:38][N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])[CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=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[N:24]([C:36](=[O:44])[CH2:37][CH2:38][N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])[CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)[CH2:19]2)=[N:16][CH:17]=1)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59367661HCID 59367661, compound

Product 1

HCID 59367590HCID 59367590, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(1-Isobutoxyethoxy) 2-{6-[(3-diethylaminopropionyl)naphthalen-2-ylmethyl-amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamide (199 mg, 0.33 mmol) was dissolved in DCM (3 ml) and treated with a solution of 4M HCl in dioxane (0.5 ml, 2 mmol). The resulting precipitate was filtered and dried to give the title compound as a white solid (94 mg, 57%). LCMS purity 98%, m/z 475 [M+H]+, 1H NMR (300 MHz, CD3OD) δ: 1.39 (6H, t, J=7.2 Hz), 2.26 (2H, br s), 2.77 (1H, s), 3.37 (4H, m), 3.55 (2H, d, J=10.5 Hz), 3.81 (4H, br s), 3.93 (2H, d, J=10.5 Hz), 4.71 (2H, br s), 7.61 (2H, m), 7.76 (1H, d, J=8.4 Hz), 7.95-8.04 (3H, m), 8.20 (1H, s), 8.71 (2H, s).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-ef2f7ff3efaf4b2bbdd7e4dc5a2e6d78
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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