Diisopropylethylamine → HCID 86729623, compound

HRID 2284895Notes

Reaction equation

HRID 2284895 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[C:5]([Cl:10])=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[NH2:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][C@H:23]([C:27]([NH2:29])=[O:28])[CH2:22]1.C(OCC)(=O)C.CCCCCC>C(O)(C)C>[Cl:10][C:5]1[C:6]([S:8][CH3:9])=[N:7][C:2]([NH:20][C@@H:21]2[CH2:26][CH2:25][CH2:24][C@H:23]([C:27]([NH2:29])=[O:28])[CH2:22]2)=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 21226206Ethyl acetate hexaneHCID 25324696HCID 25324696, compoundHCID 582009271245830-98-1

Product 1

HCID 86729623HCID 86729623, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of Intermediate 1 (2 g, 10.36 mmol) in isopropyl alcohol (10 mL), was added DIPEA (4.01 g, 31.08 mmol) and Cis-3-aminocyclohexanecarboxamide (2.2 g, 15.45 mmol) at room temperature and heated to 100° C. for 48 h in a sealed tube. TLC showed completion of starting material and formation of a polar spot (TLC System: 10% ethyl acetate/hexane, (Rf): 0.1). After cooling down to room temperature, the mixture was concentrated, water (30 ml) was added, and the precipitated product was filtered, washed with pentane (20 ml) and dried to afford Cis-3-(5-chloro-4-(methylthio)pyrimidin-2-ylamino)cyclohexanecarboxamide as a white solid (2.2 g, 70.9%). MS m/z: 301.1 (ES+, M+H).

Workup

  1. temperatureAfter cooling down to room temperature
  2. concentrationthe mixture was concentrated
  3. additionwater (30 ml) was added
  4. filtrationthe precipitated product was filtered
  5. washwashed with pentane (20 ml)
  6. customdried

Sources & evidence

ORD record
ord-ba901bbd0fe4497d857f054d31507538
Source dataset
uspto-grants-2015_09
Patent number
US09145387B2

Reaction notes

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