Cyclopropylamine → HCID 58973060, compound

HRID 19498Notes

Reaction equation

HRID 19498 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[NH:13][C:14]2[CH:15]=[C:16]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:17]=[CH:18][C:19]=2[CH3:20])[CH:3]=1.[CH:30]1([NH2:33])[CH2:32][CH2:31]1>CC(O)C>[CH:30]1([NH:33][C:2]2[N:7]=[CH:6][N:5]=[C:4]([N:8]3[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][C:14]3[CH:15]=[C:16]([NH:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:17]=[CH:18][C:19]=3[CH3:20])[CH:3]=2)[CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 58973158HCID 58973158, compound

Product 1

HCID 58973060HCID 58973060, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of N-{3-[1-(6-chloro-pyrimidin-4-yl)-1H-imidazol-2-ylamino]-4-methyl-phenyl}-benzamide (2.65 g, 6.55 mmol), cyclopropylamine (8.8 mL, 124.43 mmol) in 2-propanol (30 mL) was heated at 65° C. for 16 h. The reaction mixture was then cooled down to room temperature and concentrated. The residue yellow solid was washed with water, dried under vacuum to afford the title compound. The obtained crude title compound was directly used for the next step reaction without any further purification. 1H NMR 600 MHz (DMSO-d6) δ 11.13 (bs, 1H), 10.24 (s, 1H), 8.77 (s, 1H), 8.48 (bs, 1H), 8.10 (bs, 1H), 7.98 (d, 2H, J=6.0 Hz), 7.71 (bs, 1H), 7.57 (s, 1H), 7.52 (s, 2H), 7.34 (d, 1H, J=6.6 Hz), 7.15 (d, 1H, J=6.6 Hz), 6.88 (s, 1H), 6.74 (bs, 1H), 2.61 (bs, 1H), 2.33 (s, 3H), 0.82 (s, 2H), 0.53 (s, 2H); MS m/z 426.5 (M+1).

Workup

  1. temperatureThe reaction mixture was then cooled down to room temperature
  2. concentrationconcentrated
  3. washThe residue yellow solid was washed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f2162d80bb994642b5fa07ae344b99c2
Source dataset
uspto-grants-2010_06
Patent number
US07745437B2

Reaction notes

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