Acryloyl chloride → HCID 178460285, compound

HRID 577684Notes

Reaction equation

HRID 577684 reaction equation
[NH2:1][C@H:2]1[CH2:5][C@H:4]([NH:6][C:7]2[C:8]3[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:9]=3[N:10]=[C:11]([NH:13][C:14]3[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=3)[N:12]=2)[CH2:3]1.CCN(C(C)C)C(C)C.[C:40](Cl)(=[O:43])[CH:41]=[CH2:42]>C(Cl)Cl>[CH3:19][N:17]1[CH:18]=[C:14]([NH:13][C:11]2[N:12]=[C:7]([NH:6][C@H:4]3[CH2:3][C@H:2]([NH:1][C:40](=[O:43])[CH:41]=[CH2:42])[CH2:5]3)[C:8]3[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:9]=3[N:10]=2)[CH:15]=[N:16]1

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 178480792HCID 178480792, compound

Product 1

HCID 178460285HCID 178460285, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N4-((trans)-3-aminocyclobutyl)-N2-(1-methyl-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine (87 mg, 0.2 mmol) was dissolved in DCM (5 mL). DIPEA (53 μL, 0.3 mmol) was added and the reaction was cooled to 0° C. Acryloyl chloride (16 μL, 0.2 mmol) was added via a 10 μL syringe and the reaction was allowed to stir at 0° C. for 1 hr. The reaction was concentrated and purified via flash chromatography eluting with a gradient of 1%-20% EtOH in DCM. The fractions containing the product were pooled and dried down to afford the title compound as a tan solid (confirmed to be product by LCMS). This tan solid was taken directly to the final step.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified via flash chromatography
  3. washeluting with a gradient of 1%-20% EtOH in DCM
  4. additionThe fractions containing the product
  5. customdried down

Sources & evidence

ORD record
ord-a0a6ee8a6b3a41d7a575c4e01e82f553
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

Loading…