Diisopropylethylamine → 4-[(2-cyclopentyl-4,4,6-trimethyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-3-methoxy-N-[1-(2-methoxyethyl)-4-piperidyl]benzamide

HRID 2234292Notes

Reaction equation

HRID 2234292 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25]1([N:30]2[CH2:40][C:39]([CH3:42])([CH3:41])[C:38](=[O:43])[N:37]([CH3:44])[C:36]3[C:31]2=[N:32][C:33]([NH:45][C:46]2[CH:54]=[CH:53][C:49]([C:50](O)=[O:51])=[CH:48][C:47]=2[O:55][CH3:56])=[N:34][CH:35]=3)[CH2:29][CH2:28][CH2:27][CH2:26]1.CCN(C(C)C)C(C)C.[NH2:66][CH:67]1[CH2:72][CH2:71][N:70]([CH2:73][CH2:74][O:75][CH3:76])[CH2:69][CH2:68]1>CC(N(C)C)=O>[CH:25]1([N:30]2[CH2:40][C:39]([CH3:41])([CH3:42])[C:38](=[O:43])[N:37]([CH3:44])[C:36]3[C:31]2=[N:32][C:33]([NH:45][C:46]2[CH:54]=[CH:53][C:49]([C:50]([NH:66][CH:67]4[CH2:72][CH2:71][N:70]([CH2:73][CH2:74][O:75][CH3:76])[CH2:69][CH2:68]4)=[O:51])=[CH:48][C:47]=2[O:55][CH3:56])=[N:34][CH:35]=3)[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 201191211-(2-Methoxyethyl)piperidin-4-amineHCID 426107874-(9-cyclopentyl-5,7,7-trimethyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid2×

Product 1

HCID 686833104-[(2-cyclopentyl-4,4,6-trimethyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-3-methoxy-N-[1-(2-methoxyethyl)-4-piperidyl]benzamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

A solution of HATU (126 mg, 0.33 mmol) in DMA (5 mL) was added to a mixture of 4-[(2-cyclopentyl-4,4,6-trimethyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-3-methoxy-benzoic acid (Example 242 132 mg, 0.3 mmol), DIPEA (261 uL, 1.5 mmol) and 4-amino N-(2-methoxyethyl)piperidine (60 mg, 0.375) in DMA (5 mL). The resulting mixture was stirred at room temperature for 2 hours, then partially purified by SCX. The compound was retrieved from the SCX column using 7N ammonia in methanol, then concentrated in vacuo, and further purified by column chromatography, eluting with 0-10% ammonia (7N in methanol) in DCM. The pure material was recovered as an orange oil, which foamed and solidified under high vacuum. Trituration under ether gave a pale yellow amorphous solid. (55 mg, 32%)

Workup

  1. custompartially purified by SCX
  2. concentrationconcentrated in vacuo
  3. customfurther purified by column chromatography
  4. washeluting with 0-10% ammonia (7N in methanol) in DCM
  5. customThe pure material was recovered as an orange oil, which
  6. customTrituration under ether gave a pale yellow amorphous solid

Sources & evidence

ORD record
ord-4eee69b924d4483597b5df0973336887
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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