Diisopropylethylamine → HCID 10271171, compound

HRID 1815922Notes

Reaction equation

C[N:2]1[CH:7]=[N:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)=[N:4][CH:3]1Cl.[CH3:17]CN(C(C)C)C(C)C.[NH2:26][C:27]1[CH:28]=[C:29]([NH:33][C:34](=[O:37])[CH:35]=[CH2:36])[CH:30]=[CH:31][CH:32]=1>>[Cl:15][C:11]1[CH:10]=[C:9]([N:8]([CH3:17])[C:5]2[N:6]=[CH:7][N:2]=[C:3]([NH:26][C:27]3[CH:28]=[C:29]([NH:33][C:34](=[O:37])[CH:35]=[CH2:36])[CH:30]=[CH:31][CH:32]=3)[N:4]=2)[CH:14]=[CH:13][CH:12]=1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 22028112HCID 22028112, compound

HCID 22033841N-(3-Aminophenyl)acrylamide

Product 1

HCID 10271171HCID 10271171, compound

Conditions

Temperature: 100 °C

Procedure

To a slurry of N-methyl-2-chloro-4-(3-chloroanilino)-1,3,5-triazine (Step 1) (44.6 mg, 0.175 mmol) in IpOH (2.0 ml) was added DIEA (0.046 mL, 0.26 mmol) and N-(3-aminophenyl)acrylamide (31 mg, 0.192 mmol). The mix was heated at 100° C. for 18 h. The solution was then cooled to RT. The organics were concentrated under reduced pressure and the crude product was purified via column chromatography (elution with EtOAc) to give N-(3-{4-[(3-chlorophenyl)-methyl-amino]-[1,3,5]triazin-2-ylamino}-phenyl)-acrylamide: MS m/z=381 [M+H]+. Calc'd for C19H17ClN6O: 380.12.

Workup

temperatureThe solution was then cooled to RT
concentrationThe organics were concentrated under reduced pressure
customthe crude product was purified via column chromatography (elution with EtOAc)

Sources & evidence

ORD record: ord-c110b5055f774506950fe76531fcbd31
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881737B2

Reaction notes

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