Potassium Carbonate → HCID 68787026, compound

HRID 2093608Notes

Reaction equation

HRID 2093608 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:28]([CH3:30])[CH3:29])[C:6]2[O:10][C:9]([C:11]3[CH:26]=[CH:25][C:14]([C:15]([NH:17][CH2:18][C@H:19]4[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:27]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:48])([F:47])[F:46])[CH:40]=1>CO>[C:1]([C:3]1[CH:4]=[C:5]([CH:28]([CH3:30])[CH3:29])[C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([NH:17][CH2:18][C@H:19]4[CH2:24][CH2:23][CH2:22][N:21]([CH2:38][C:39]5[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:46])([F:47])[F:48])[CH:40]=5)[CH2:20]4)=[O:16])=[CH:25][CH:26]=3)=[N:8][C:7]=2[CH:27]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 68745182HCID 68745182, compound

Product 1

HCID 68787026HCID 68787026, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(5-Cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-[(3S)-piperidin-3-ylmethyl]benzamide (20 mg) was taken up in methanol (3 ml) and then potassium carbonate (14 mg) and 1-(bromomethyl)-3-(trifluoromethyl)benzene (14 □l) were added. The mixture was stirred for 1.5 h and then added directly to a Biotage 40M samplet for purification via column chromatography on a Biotage Horizon 40M column, eluting with 1 column volume of 100% hexanes followed by a gradient of 0 to 100% ethyl acetate in hexanes over 10 column volumes to provide the title compound (20 mg, 71%). Mass spectrum (ESI) 561.4 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.31 (d, J=8.4 Hz, 1H), 7.95 (s, 1H), 7.85 (d, J=8.4 Hz, 2H), 7.59 (s, 1H), 7.55 (m, 3H), 7.41 (t, J=7.7 Hz, 2H), 6.43 (t, J=5.8 Hz, 1H), 3.47 (m, 3H), 2.72 (m, 3H), 2.34 (s, 3H), 2.03 (m, 2H), 1.90 (t, J=11.4 Hz, 2H), 1.47 (d, J=6.9 Hz, 6H), 1.31 (m, 1H).

Workup

  1. additionadded directly to a Biotage 40M
  2. customsamplet for purification via column chromatography on a Biotage Horizon 40M column
  3. washeluting with 1 column volume of 100% hexanes

Sources & evidence

ORD record
ord-2eee7d5a304d4d5081e35598b448ffe7
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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