Acetic Acid → HCID 57974325, compound

HRID 1864184Notes

Reaction equation

HRID 1864184 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:34](O)(=[O:36])[CH3:35].[Cl:38][C:39]1[CH:40]=[C:41]([NH:53][C:54]2[C:63]3[C:58](=[CH:59][CH:60]=[CH:61][C:62]=3[O:64][CH2:65][CH2:66][NH:67][CH3:68])[N:57]=[CH:56][N:55]=2)[CH:42]=[CH:43][C:44]=1[O:45][CH2:46]C1C=CC=CN=1>C(Cl)Cl>[Cl:38][C:39]1[CH:40]=[C:41]([CH:42]=[CH:43][C:44]=1[O:45][CH2:46][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][N:15]=1)[NH:53][C:54]1[C:63]2[C:58](=[CH:59][CH:60]=[CH:61][C:62]=2[O:64][CH2:65][CH2:66][N:67]([CH3:68])[C:34](=[O:36])[CH3:35])[N:57]=[CH:56][N:55]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69065361N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine

Product 1

HCID 57974325HCID 57974325, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of HATU (197 mg), diisopropylethylamine (90 μl), acetic acid (22 μl) and N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine (150 mg) in DCM (20 ml) was stirred for 2 hours. The solution washed with water, then brine and concentrated in vacuo. The residue was purified by chromatography using DCM—5% methanol as eluent to give the title compound as a white solid (114 mg, 69%); NMR spectrum (DMSO-d6) 1.95 (s, 3H), 3.00 (s, 3H), 3.89 (t, 2H), 4.48 (m, 2H), 5.29 (s, 2H), 7.18 (d, 1H), 7.24 (d, 1H), 7.35 (m, 2H), 7.59 (m, 2H), 7.72 (dd, 1H), 7.85 (dt, 1H), 7.96 (d, 1H), 8.46 (s, 1H), 8.58 (m, 1H), 9.70 (bs, 1H); Mass spectrum MH+ 478.5.

Workup

  1. washThe solution washed with water
  2. concentrationbrine and concentrated in vacuo
  3. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-4aa184f719ab4536a87fb628212d5cc5
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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