Diisopropylethylamine → HCID 10223056, compound

HRID 1815925Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2[C:12]2[N:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[NH2:28][C:29]1[CH:30]=[C:31]([NH:35][C:36](=[O:39])[CH:37]=[CH2:38])[CH:32]=[CH:33][CH:34]=1>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2[C:12]2[N:13]=[CH:14][N:15]=[C:16]([NH:28][C:29]3[CH:30]=[C:31]([NH:35][C:36](=[O:39])[CH:37]=[CH2:38])[CH:32]=[CH:33][CH:34]=3)[N:17]=2)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 22033841N-(3-Aminophenyl)acrylamide

HCID 22496109HCID 22496109, compound

Product 1

HCID 10223056HCID 10223056, compound

Conditions

Temperature: 100 °C

Procedure

To a slurry of 7-chloro-1-(4-chloro-[1,3,5]triazin-2-yl)-1,2,3,4-tetrahydro-quinoline (Step 2)(70 mg, 0.249 mmol) in IpOH (2.0 ml) was added DIEA (0.20 mL, 1.15 mmol) and N-(3-aminophenyl)acrylamide (100 mg, 0.192 mmol). The heated at 100° C. for 18 h, then cooled to RT. The organics were concentrated under reduced pressure then purified by column chromatography (elution with CH2Cl2 followed by 99:1 CH2Cl2/MeOH followed by 97:3 CH2Cl2/MeOH) to give N-{3-[4-(7-chloro-3,4-dihydro-2H-quinolin-1-yl)-[1,3,5]triazin-2-ylamino]-phenyl}-acrylamide: MS m/z=407 [M+H]+. Calc'd for C21H19ClN6O: 406.13.

Workup

temperaturecooled to RT
concentrationThe organics were concentrated under reduced pressure
customthen purified by column chromatography (elution with CH2Cl2 followed by 99:1 CH2Cl2/MeOH followed by 97:3 CH2Cl2/MeOH)

Sources & evidence

ORD record: ord-c4386dd81e464d48add07cdb21533274
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881737B2

Reaction notes

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