Methanol → HCID 86729632, compound

HRID 2284904Notes

Reaction equation

HRID 2284904 reaction equation
[C:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[C:18]([C:19]([NH:21][CH3:22])=[O:20])=[CH:17][N:16]=[C:15](Cl)[N:14]=1)(=[O:4])[CH:2]=[CH2:3].[CH3:24][O:25][C:26]1[CH:32]=[C:31]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH:30]=[CH:29][C:27]=1[NH2:28].CO>CC1C=CC(S(O)(=O)=O)=CC=1.O1CCOCC1.C(Cl)Cl>[C:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[C:18]([C:19]([NH:21][CH3:22])=[O:20])=[CH:17][N:16]=[C:15]([NH:28][C:27]2[CH:29]=[CH:30][C:31]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[CH:32][C:26]=2[O:25][CH3:24])[N:14]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 4149602-Methoxy-4-morpholinoanilineHCID 86729631HCID 86729631, compound

Product 1

HCID 86729632HCID 86729632, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 86729633HCID 86729633, compoundSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(2-acrylamidophenylamino)-2-chloro-N-methylpyrimidine-5-carboxamide (40 mg, 0.12 mmol) in 0.08M p-TSA/1,4-dioxane (5 mL), 2-methoxy-4-morpholinoaniline (25.13 mg, 0.12 mmol) was added and heated at 100° C. for 1 h. TLC showed completion of starting material (TLC system: 5% methanol in DCM (Rf): 0.3). 1,4 dioxane was evaporated, and the residue was diluted with ethyl acetate (15 mL) and washed with water (2×5 mL). The organic layer was separated, dried over sodium sulphate, and concentrated. Crude compound was purified by column chromatography using silica gel (100-200 mesh) with 2% methanol in DCM to obtain 4-(2-acrylamidophenylamino)-2-(2-methoxy-4-morpholino phenylamino)-N-methylpyrimidine-5-carboxamide as off white solid. Yield: (8 mg, 13%). MS: m/z 504.3 (ES+, M+H).

Workup

  1. custom1,4 dioxane was evaporated
  2. additionthe residue was diluted with ethyl acetate (15 mL)
  3. washwashed with water (2×5 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customCrude compound was purified by column chromatography

Sources & evidence

ORD record
ord-36f03646b25a48d9a2b7ec4d91ec68d5
Source dataset
uspto-grants-2015_09
Patent number
US09145387B2

Reaction notes

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