HCID 58654411, compound → HCID 68691008, compound

HRID 1170486Notes

Reaction equation

HRID 1170486 reaction equation
C(OC(=O)[N:7]([CH2:25][C:26]1[CH:34]=[CH:33][C:29]2[O:30][CH2:31][O:32][C:28]=2[CH:27]=1)[CH2:8][CH2:9][NH:10][CH:11]([C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)[N:14]=1)[CH3:12])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[O:30]1[C:29]2[CH:33]=[CH:34][C:26]([CH2:25][NH:7][CH2:8][CH2:9][NH:10][CH:11]([C:13]3[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([N:20]4[CH:24]=[CH:23][N:22]=[CH:21]4)[N:14]=3)[CH3:12])=[CH:27][C:28]=2[O:32][CH2:31]1

Participants

3

Reactant 1

HCID 58654411HCID 58654411, compound

Product 1

HCID 68691008HCID 68691008, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of benzo[1,3]dioxol-5-ylmethyl-{2-[1-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-ethylamino]-ethyl}-carbamic acid tert-butyl ester (155 mg, 0.320 mmol) in DCM/TFA (50%, 5 mL) was stirred for 0.5 h. The solvent was evaporated and sat. aqueous K2CO3 solution was added. The mixture was extracted with ethyl acetate, washed with brine and dried over Na2SO4. Evaporation of the solvent gave 110 mg (90%) of N-benzo[1,3]dioxol-5-ylmethyl-N′-[1-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-ethyl]-ethane-1,2-diamine as a red oil. [M+H]+ 380.96; 1H-NMR (400 MHz, CDCl3) δ 8.59 (s, 1H), 7.87 (s, 1H), 7.09 (s, 1H), 7.05 (s, 1H), 6.79 (s, 1H), 6.71 (s, 2H), 5.90 (s, 2H), 3.74 (q, 1H), 3.66 (s, 2H), 2.70-2.50 (m, 6H), 2.2 (br s, 2H), 1.37 (d, 3H); 13C-NMR (100 MHz, CDCl3) δ 175.6, 170.0, 154.6, 147.9, 146.8, 136.4, 134.2, 130.5, 121.4, 116.8, 115.6, 108.8, 108.3, 101.1, 58.8, 53.8, 48.9, 47.4, 24.4, 22.4.

Workup

  1. customThe solvent was evaporated
  2. additionsat. aqueous K2CO3 solution was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3f18ae0d1aed43d8a17b474c04205c00
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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