Diisopropylethylamine → HCID 86636621, compound

HRID 2381701Notes

Reaction equation

HRID 2381701 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.CCN(C(C)C)C(C)C.[NH2:21][C:22]1[CH:23]=[C:24]([CH:31]=[CH:32][CH:33]=1)[O:25][CH2:26][C:27]([NH:29][CH3:30])=[O:28]>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:23]=[C:24]([CH:31]=[CH:32][CH:33]=2)[O:25][CH2:26][C:27]([NH:29][CH3:30])=[O:28])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidineHCID 22060559N-Methyl 3-aminophenoxyacetamide

Product 1

HCID 86636621HCID 86636621, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine (0.062 g, 0.33 mmol) in DMSO (1 mL) was added DIPEA (0.117 mL, 0.66 mmol) and 2-(3-aminophenoxy)-N-methylacetamide (0.095 g, 0.49 mmol). After heating at 100° C. for 15 h, it was diluted with EtOAc, washed with saturated NaHCO3, brine, dried and concentrated to give 2-(3-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)phenoxy-N-methylacetamide (0.062 g).

Workup

  1. washwashed with saturated NaHCO3, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5173068e41db49ee9e706ba0b44d43e4
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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