Hydrochloric Acid → N-(3,4-dimethoxyphenethyl)-4-(6-methoxy-4-(piperazin-1-yl)naphthalen-2-yl)pyrimidin-2-amine

HRID 1921972Notes

Reaction equation

HRID 1921972 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:40]=[CH:41][C:42]=1[O:43][CH3:44])[CH2:6][CH2:7][NH:8][C:9]1[N:14]=[C:13]([C:15]2[CH:16]=[C:17]([N:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]3)[C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[C:20]([O:25][CH3:26])[CH:19]=3)[CH:12]=[CH:11][N:10]=1.Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:40]=[CH:41][C:42]=1[O:43][CH3:44])[CH2:6][CH2:7][NH:8][C:9]1[N:14]=[C:13]([C:15]2[CH:16]=[C:17]([N:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]3)[C:18]3[C:23](=[CH:22][CH:21]=[C:20]([O:25][CH3:26])[CH:19]=3)[CH:24]=2)[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67306106HCID 67306106, compound

Product 1

HCID 67305590N-(3,4-dimethoxyphenethyl)-4-(6-methoxy-4-(piperazin-1-yl)naphthalen-2-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound (109) was dissolved in methanol (2 mL) and charged with HCl (1 mL, 4 M solution in dioxane). The resulting mixture was stirred at room temperature for 16 h. It was then filtered and dried under high vacuum to afford N-(3,4-dimethoxyphenethyl)-4-(6-methoxy-4-(piperazin-1-yl)naphthalen-2-yl)pyrimidin-2-amine (110) as a yellow solid (0.125 g). M.p.=138-140° C. 400 MHz 1H NMR (DMSO-d6) δ: 9.36 (br s, 2H), 8.44-8.43 (m, 2H), 8.02 (d, J=9.0 Hz, 1H), 7.86 (s, 1H), 7.52 (s, 1H), 7.43 (s, 1H), 7.31 (d, J=6.3 Hz, 1H), 6.92-6.82 (m, 3H), 3.97 (s, 3H), 3.73-3.68 (m, 8H), 3.41-3.31 (m, 8H), 2.89 (m, 2H); Experimental Elemental Analysis (2.9 equivalents of HCl)=57.53% C, 5.90% H, 11.37% N; Calculated Elemental Analysis 57.54% C, 5.98% H, 11.57% N; LCMS (m/z): 500 [M+H].

Workup

  1. filtrationIt was then filtered
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-bd0e4c54dc254c1096ab6827ce74b05f
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

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