HCID 4271606, compound → HCID 44206773, compound

HRID 2401948Notes

Reaction equation

HRID 2401948 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13](Cl)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[Cl:16][C:17]1[CH:32]=[CH:31][C:20]([O:21][CH:22]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH2:30])[N:25]=2)[CH3:23])=[CH:19][CH:18]=1>N1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:30][C:26]4[N:25]=[C:24]([CH:22]([O:21][C:20]5[CH:31]=[CH:32][C:17]([Cl:16])=[CH:18][CH:19]=5)[CH3:23])[CH:29]=[CH:28][N:27]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 4271606HCID 4271606, compoundHCID 591291541-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride

Product 1

HCID 44206773HCID 44206773, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

To 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (45 mg, 0.2 mmol) in pyridine (2 mL) was added 4-(1-(4-chlorophenoxy)ethyl)pyrimidin-2-amine (50 mg, 0.2 mmol) and the reaction mixture was stirred at 115° C. for 15 hours. The solvent was evaporated to dryness and the residue redissolved in DMF, filtered and purified by reverse-phase preparative liquid chromatography utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoracetic acid to yield the pure product. ESI-MS m/z calc. 437.9, found 438.1 (M+1)+. Retention time 3.16 minutes.

Workup

  1. customThe solvent was evaporated to dryness
  2. dissolutionthe residue redissolved in DMF
  3. filtrationfiltered
  4. custompurified by reverse-phase preparative liquid chromatography
  5. customto yield the pure product

Sources & evidence

ORD record
ord-7121869ce3b34d98827728c0ce170db5
Source dataset
uspto-grants-2014_08
Patent number
US08796312B2

Reaction notes

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