Dimethylacetamide → HCID 57531473, compound

HRID 1091930Notes

Reaction equation

Cl[C:2]1[C:7]([CH2:8][N:9]([CH3:20])[C@@H:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[C:6]([CH3:21])[N:5]=[C:4]([C:22]2[C:27]([CH2:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:30][CH3:31])[N:3]=1.CC(N(C)C)=O.[O:38]1[C:42]2([CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[O:41][CH2:40][CH2:39]1.C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH2:28]([C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:30][CH3:31])[C:22]=1[C:4]1[N:3]=[C:2]([N:45]2[CH2:46][CH2:47][C:42]3([O:41][CH2:40][CH2:39][O:38]3)[CH2:43][CH2:44]2)[C:7]([CH2:8][N:9]([CH3:20])[C@@H:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[C:6]([CH3:21])[N:5]=1)[CH3:29]

Participants

Conditions

Temperature: 85 °C

Procedure

To a vial containing [4-chloro-2-(2,6-diethyl-phenyl)-6-methyl-pyrimidin-5-ylmethyl]-methyl-(1S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine (1.0 mL of a 0.2M DMA solution, 0.2 mmol) is added 1,4-dioxa-8-azaspiro(4,5)decane (1.0 ml of a 1.0M DMA solution, 5.0 eq.) and the resulting solution is vortex heated at 85° C. for 12 h. Once the reaction has cooled to room temperature, EtOAc (1.0 mL) and sat NaHCO3 (1.0 mL) is added and the organic layer is plated directly onto a SiO2 preparatory chromatography plate and the product is eluted using hexanes:Et2O 1:1, which affords the title compound as a colorless oil. [mass expected (540.74); mass found (540.43)].

Workup

temperatureOnce the reaction has cooled to room temperature
additionis added
washthe product is eluted

Sources & evidence

ORD record: ord-cee70841eef5440196e122300ae2dd1b
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129395B2

Reaction notes

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