Dichloromethane → HCID 57974285, compound

HRID 1864347Notes

Reaction equation

HRID 1864347 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].Cl[C:6]1[CH:7]=[C:8]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][C:29]=3[O:31][CH2:32][CH2:33][NH:34][CH3:35])[N:24]=[CH:23][N:22]=2)[CH:9]=C[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[CH2:36]([Cl:38])Cl>>[Cl:38][C:36]1[CH:9]=[C:8]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][C:29]=3[O:31][CH2:32][CH2:33][N:34]([CH3:35])[C:3]([NH:2][CH3:1])=[O:4])[N:24]=[CH:23][N:22]=2)[CH:7]=[CH:6][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 12228Methyl IsocyanateHCID 69065361N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine

Product 1

HCID 57974285HCID 57974285, compoundYield 83%

Procedure

Methyl isocyanate (0.035 ml) was added slowly to a stirred solution of N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine (obtained as described in Example 1, preparation of starting materials, 217 mg) in DCM (10 ml). The resulting solution was stirred for 2 hours and then evaporated. The residue was triturated with acetonitrile and the resulting solid washed with ether to give the title compound as a solid (205 mg, 83%); NMR spectrum (DMSO-d6 @ 373K) 2.85 (s, 3H), 2.95 (s, 3H), 3.75-3.85 (t, 2H), 4.35-4.45 (t, 2H), 5.25 (s, 2H), 5.90-6.00 (bs, 1H), 7.10-7.15 (d, 1H), 7.15-7.25 (d, 1H), 7.30-7.37 (t, 2H), 7.52-7.60 (m, 2H), 7.65-7.73 (t, 1H), 7.80-7.86 (m, 1H), 7.94-7.99 (d, 1H), 8.44 (s, 1,H), 8.55-8.60 (d, 1H), 9.80 (s, 1H); Mass spectrum MH+ 493.4.

Workup

  1. customevaporated
  2. customThe residue was triturated with acetonitrile
  3. washthe resulting solid washed with ether

Sources & evidence

ORD record
ord-e22f46a1c4fa4d69b94ade261ee9d5b5
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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