Hexane → HCID 19783397, compound

HRID 257522Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8][C:9]3[C:10]([N:15]=2)=[N:11][CH:12]=[CH:13][CH:14]=3)[CH:2]=1.CCCCCC.[H-].[Na+].Br[CH2:25][C:26]1[CH:43]=[CH:42][C:29]([C:30]([N:32]([CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[CH:33]([CH3:35])[CH3:34])=[O:31])=[CH:28][C:27]=1[O:44][CH3:45]>CC(N(C)C)=O>[CH:36]1([N:32]([CH:33]([CH3:35])[CH3:34])[C:30](=[O:31])[C:29]2[CH:42]=[CH:43][C:26]([CH2:25][N:11]3[CH:12]=[CH:13][CH:14]=[C:9]4[N:8]=[C:7]([C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)[N:15]=[C:10]34)=[C:27]([O:44][CH3:45])[CH:28]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

Conditions

Temperature: 25 °C

Procedure

2-(3-Pyridyl)-1H imidazo(4,5-b)pyridine (1.3 g, 6.6 mmol) was added to a hexane-washed suspension of NaH (175 mg, 7.26 mmol) in dimethylacetamide (15 ml) under Ar and stirred under an argon atomsphere for one hour at 25° C. 4-Bromomethyl-3-methoxy-N-cyclohexyl-N-isopropylbenzamide (2.5 g, 6.6 mmol) was added portionwise over 30 minutes and the mixture stirred overnight at 25° C. The solvent was removed via oil pump at <50° C. and the residue was chromatographed using 7/3/0.5 CH2Cl2 /MeOH/NH4OH as the eluent to produce the title compound (1.70 g, 52%). An analytical sample was prepared by recrystallization from ethyl acetate, m.p. 185°-188° C. Anal. Calc. for C29H33N5O2.0.5H2O: C, 70.71; H, 6.96; N, 14.22. Found: C, 70.88; H, 6.80; N, 14.18.

Workup

washwashed
stirringthe mixture stirred overnight at 25° C
customThe solvent was removed via oil pump at <50° C.
customthe residue was chromatographed

Sources & evidence

ORD record: ord-b534fc6886e24e10b9690e5d9738627b
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05262426

Reaction notes

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