HCID 58065786, compound → HCID 56644723, compound

HRID 2370948Notes

Reaction equation

HRID 2370948 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:7][CH:6]([NH:8][C:9]2[C:14]([C:15]([NH2:17])=[O:16])=[CH:13][N:12]=[C:11](Cl)[N:10]=2)[CH2:5][C:4]([CH3:20])([CH3:19])[NH:3]1.[CH:22]1([C:25]2[C:30]([N:31]3[CH:35]=[N:34][N:33]=[N:32]3)=[CH:29][C:28]([NH2:36])=[C:27]([F:37])[CH:26]=2)[CH2:24][CH2:23]1>CC(O)C>[CH3:1][C:2]1([CH3:21])[CH2:7][CH:6]([NH:8][C:9]2[C:14]([C:15]([NH2:17])=[O:16])=[CH:13][N:12]=[C:11]([NH:36][C:28]3[CH:29]=[C:30]([N:31]4[CH:35]=[N:34][N:33]=[N:32]4)[C:25]([CH:22]4[CH2:23][CH2:24]4)=[CH:26][C:27]=3[F:37])[N:10]=2)[CH2:5][C:4]([CH3:20])([CH3:19])[NH:3]1

Participants

4

Reactant 2

HCID 58065786HCID 58065786, compoundHCID 58065809HCID 58065809, compound

Product 1

HCID 56644723HCID 56644723, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(2,2,6,6-tetramethylpiperidin-4-ylamino)-2-chloropyrimidine-5-carboxamide (178 mg, 0.570 mmol, 1 equiv), 4-cyclopropyl-2-fluoro-5-(1H-tetrazol-1-yl)benzenamine (150 mg, 0.684 mmol, 1.2 equiv), and PTSA monohydrate (230 mg, 1.20 mmol, 2.1 equiv) in IPA (6 mL) were heated to 100° C. overnight giving a precipitate. The precipitate was collected by vacuum filtration and rinsed with IPA. The solid was taken in EtOAc then adjusted to ca. pH 12-14 with 1N NaOH. The aqueous and organic layers were partitioned. The aqueous layer was extracted with EtOAc (2×150 mL). The combined organics were washed with 1N NaOH (1×150 mL), dried (Na2SO4), filtered, and concentrated to give the desired product (128 mg, 50%) as a solid.

Workup

  1. customgiving a precipitate
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washrinsed with IPA
  4. customThe aqueous and organic layers were partitioned
  5. extractionThe aqueous layer was extracted with EtOAc (2×150 mL)
  6. washThe combined organics were washed with 1N NaOH (1×150 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e5b7dbbe750f432d89e7df6efa3b158d
Source dataset
uspto-grants-2014_04
Patent number
US08710223B2

Reaction notes

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