Pyridine → HCID 44600124, compound

HRID 1968642Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH2:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].[N:21]1[CH:26]=[CH:25]C=C[CH:22]=1.Cl[C:28](OC1C=CC=CC=1)=[O:29].COC(OC)CNC>CN(C=O)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N:20]4[CH:25]=[CH:26][N:21]([CH3:22])[C:28]4=[O:29])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N4-(3-ethynylphenyl)quinazoline-4,6-diamine (100 mg, 0.38 mmol) in DMF (2 mL) containing pyridine (37 μL, 0.46 mmol) was added phenyl chloroformate (49 μL, 0.38 mmol) dropwise at room temperature. After 10 min, (methylamino)acetaldehyde dimethylacetal (45.2 mg, 0.38 mmol) was added and the reaction mixture was heated to 100° C. for 1 h. After cooled to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The combined organic layers were concentrated and purified with a silica column to give Compound 126 as a yellow solid in 83% yield.

Workup

temperatureAfter cooled to room temperature
washwashed with water
concentrationThe combined organic layers were concentrated
custompurified with a silica column

Sources & evidence

ORD record: ord-419b185c28db41819b35c7acde6f700c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426430B2

Reaction notes

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