Acetic Acid → HCID 178457303, compound

HRID 518631Notes

Reaction equation

HRID 518631 reaction equation
[C:1]([C@@H:4]1[CH2:9][CH2:8][C@H:7]([N:10]2[C:14]3[CH:15]=[C:16]([CH2:19][N:20]4[CH2:25][CH2:24][CH:23]([C:26]([OH:29])([CH3:28])[CH3:27])[CH2:22][CH2:21]4)[CH:17]=[CH:18][C:13]=3[NH:12]/[C:11]/2=[N:30]\[C:31](=[O:39])[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=2)[CH2:6][CH2:5]1)(=O)[CH3:2].[CH3:40][CH:41]([NH2:43])[CH3:42].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O>ClC(Cl)C>[F:38][C:34]1[CH:33]=[C:32]([CH:37]=[CH:36][CH:35]=1)[C:31](/[N:30]=[C:11]1\[NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:25][CH2:24][CH:23]([C:26]([OH:29])([CH3:27])[CH3:28])[CH2:22][CH2:21]3)=[CH:15][C:14]=2[N:10]\1[C@H:7]1[CH2:8][CH2:9][C@@H:4]([CH:1]([NH:43][CH:41]([CH3:42])[CH3:40])[CH3:2])[CH2:5][CH2:6]1)=[O:39]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6363IsopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178468172HCID 178468172, compound

Product 1

HCID 178457303HCID 178457303, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

(E)-N-(1-(cis-4-acetylcyclohexyl)-6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-1H-benzo[d]imidazol-2(3H)-ylidene)-3-fluorobenzamide (0.06 g, 0.112 mmol) was suspended in 0.37 mL of dichloroethane. To this mixture was added propan-2-amine (7.30 mg, 0.123 mmol) followed by sodium triacetoxyborohydride (0.033 g, 0.157 mmol) and AcOH (6.42 pt, 0.112 mmol). The resulting mixture was stirred for 6 hours at RT and quenched with 1N aqueous NaOH (5 mL). DCM (20 mL) was added and the layers were separated. The organic portion was dried over sodium sulfate and concentrated to afford a yellow residue which was purified by silica gel chromatography (5-30% MeOH/DCM) to afford (E)-3-fluoro-N-(6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-1-(cis-4-(1-(isopropylamino)ethyl)cyclohexyl)-1H-benzo[d]imidazol-2(3H)-ylidene)benzamide as an off-white solid (10 mg, 15.42% yield). MS m/z=578.4 [M+H]. Calc'd for C34H48FN5O2: 577.4

Workup

  1. customquenched with 1N aqueous NaOH (5 mL)
  2. additionDCM (20 mL) was added
  3. customthe layers were separated
  4. dry with materialThe organic portion was dried over sodium sulfate
  5. concentrationconcentrated
  6. customto afford a yellow residue which
  7. customwas purified by silica gel chromatography (5-30% MeOH/DCM)

Sources & evidence

ORD record
ord-6f1c0c6aaffe4838be1e1af5b6ce858f
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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