Methoxyacetic Acid → HCID 11225275, compound

HRID 1442987Notes

Reaction equation

HRID 1442987 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=O.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[Cl:26][C:27]1[CH:28]=[C:29]([NH:34][C:35]2[C:44]3[C:39](=[CH:40][C:41]([O:52][CH3:53])=[CH:42][C:43]=3[O:45][CH2:46][C@H:47]3[CH2:51][CH2:50][CH2:49][NH:48]3)[N:38]=[CH:37][N:36]=2)[CH:30]=[CH:31][C:32]=1[F:33]>C(Cl)Cl>[Cl:26][C:27]1[CH:28]=[C:29]([NH:34][C:35]2[C:44]3[C:39](=[CH:40][C:41]([O:52][CH3:53])=[CH:42][C:43]=3[O:45][CH2:46][C@H:47]3[CH2:51][CH2:50][CH2:49][N:48]3[C:4](=[O:6])[CH2:3][O:2][CH3:1])[N:38]=[CH:37][N:36]=2)[CH:30]=[CH:31][C:32]=1[F:33]

Participants

5

Reactant 3

HCID 12251Methoxyacetic AcidHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 68676941HCID 68676941, compound

Product 1

HCID 11225275HCID 11225275, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methoxyacetic acid (27 mg) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (103 mg) were added sequentially, each in one portion, to a stirred mixture of N-(3-chloro-4-fluorophenyl)-7-methoxy-5-[(2R)-pyrrolidin-2-ylmethoxy]-quinazolin-4-amine (100 mg) in DCM (2 ml) at room temperature. The reaction mixture was stirred for 1 hour and then diluted with DCM (10 ml) and washed with saturated aqueous sodium hydrogen carbonate. The organic layer was dried (MgSO4) and concentrated in vacuo to leave a yellow solid, which was triturated with 1:1 ether/hexanes and filtered to give the title compound as a white solid (97 mg, 82%); NMR Spectrum (DMSO-d6) 9.90 (br s, 1H), 8.40 (s, 1H), 8.15 (m, 1H), 7.65 (m, 1H), 7.40 (m, 1H), 6.80 (m, 2H), 4.60 (m, 1H), 4.50 (m, 1H), 4.25 (m, 1H), 4.0 (m, 3H), 3.95 (s, 3H), 3.50 (m, 21), 3.20 (m, 2H), 2.0-1.85 (m, 4H); Mass spectrum MH+ 475.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto leave a yellow solid, which
  5. customwas triturated with 1:1 ether/hexanes
  6. filtrationfiltered

Sources & evidence

ORD record
ord-0a0caba595634bf099feb08ae5e9b9f6
Source dataset
uspto-grants-2010_02
Patent number
US07659279B2

Reaction notes

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