Cycloheptylamine → HCID 73214115, compound

HRID 2200881Notes

Reaction equation

HRID 2200881 reaction equation
[CH:1]12[CH2:6][CH:5]1[CH2:4][N:3]([C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([Cl:23])[CH:16]=3)[C:10]([C:24]([OH:26])=O)=[CH:9][N:8]=1)[CH2:2]2.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:60]1([NH2:67])[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]1>C1COCC1>[CH:1]12[CH2:6][CH:5]1[CH2:4][N:3]([C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([Cl:23])[CH:16]=3)[C:10]([C:24]([NH:67][CH:60]3[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]3)=[O:26])=[CH:9][N:8]=1)[CH2:2]2

Participants

6

Reactant 4

HCID 2899CycloheptylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1176225452-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid

Product 1

HCID 73214115HCID 73214115, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (30 mL) were dissolved 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-(3-chloro-4-methoxybenzylamino)-pyrimidine-5-carboxylic acid (202 mg, 0.54 mmol) and DIEA (0.3 mL, 1.78 mmol). The reaction mixture was cooled in an ice bath, then HATU (250 mg, 0.65 mmol) and cycloheptanyl amine (67 mg, 0.60 mmol) were added. The react ion was conducted at ambient temperature overnight. The reaction mixture was concentrated, quenched with water and extracted with ethyl acetate. The organic phase was dried, concentrated, and purified by silica gel column chromatography (ethyl acetate/petroleum ether=3/1) to give 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-meth oxybenzyl)amino)-N-cycloheptanylpyrimidine-5-formamide (98 mg, 38.6% yield).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. concentrationThe reaction mixture was concentrated
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (ethyl acetate/petroleum ether=3/1)

Sources & evidence

ORD record
ord-67d05fab4a8b493389c958db0ff892ef
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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