Dimethylacetamide → HCID 25153106, compound

HRID 545433Notes

Reaction equation

[CH:1]1([N:4]2[C:8]([C:9]([N:11]3[CH2:16][CH2:15][CH:14]([N:17]4[CH2:21][CH2:20][CH2:19][CH2:18]4)[CH2:13][CH2:12]3)=[O:10])=[C:7]([C:22]3[CH:23]=[N:24][C:25](SC)=[N:26][CH:27]=3)[N:6]=[C:5]2[C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=2)[CH2:3][CH2:2]1.CC([N:44](C)C)=O>O.NN>[NH2:44][C:25]1[N:26]=[CH:27][C:22]([C:7]2[N:6]=[C:5]([C:30]3[CH:31]=[CH:32][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:34][CH:35]=3)[N:4]([CH:1]3[CH2:2][CH2:3]3)[C:8]=2[C:9]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[O:10])=[CH:23][N:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

0.06 g (0.1 mmol) of [3-cyclopropyl-5-(2-methylsulfanyl-pyrimidin-5-yl)-2-(4-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 88) was dissolved in 1 ml of DMA and 0.5 ml of hydrazine monohydrate. The mixture was heated to 100° C. for 24 h after which time the solvent was evaporated, then it was re-dissolved in EtOH and a generous spatula of Rainey nickel was added. The mixture was stirred for 1 h after which time it was filtered over Hyflo and concentrated. Purification by flash column chromatography [CH2Cl2/MeOH 8:2] afforded 0.01 g (17%) of the title compound as a colorless amorphous solid. MS: 542.2 (MH+).

Workup

customwas evaporated
dissolutionit was re-dissolved in EtOH
additiona generous spatula of Rainey nickel was added
filtrationwas filtered over Hyflo
concentrationconcentrated
customPurification by flash column chromatography [CH2Cl2/MeOH 8:2]

Sources & evidence

ORD record: ord-414ee71f360a4f23b2c1a9716bc44a14
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935707B2

Reaction notes

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