Diisopropylethylamine → HCID 68483185, compound

HRID 2174645Notes

Reaction equation

HRID 2174645 reaction equation
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH:19]=1)[C:16]([OH:18])=O.[CH3:20][CH:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)[CH2:23][CH2:22]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH:19]=1)[C:16]([NH:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][N:24]2[CH2:25][CH2:26][CH:21]([CH3:20])[CH2:22][CH2:23]2)=[CH:33][CH:32]=1)=[O:18]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 887075-Bromonicotinic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10849954-[(4-Methylpiperidin-1-yl)methyl]aniline

Product 1

HCID 68483185HCID 68483185, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DIEA (473 μL, 2.72 mmol) was added into a solution of 5-bromonicotinic acid (178 mg, 0.881 mmol), 4-((4-methylpiperidin-1-yl)methyl)benzenamine (150 mg, 0.734 mmol), BOP (487 mg, 1.10 mmol) in DMF (3 mL). The reaction mixture is stirred at rt under argon atmosphere overnight. The reaction mixture was diluted with 80 mL of AcOEt, and then washed with 1N NaOH aqueous solution three times. Organic phase was dried with anhydrous Na2SO4, and then evaporated to remove organic solvents. The obtained residue was further dried under high vacuum overnight to give crude product, which was used directly for the next step synthesis without further purification. MS (ESI+) m/z 388.1 [M+H]+.

Workup

  1. washwashed with 1N NaOH aqueous solution three times
  2. dry with materialOrganic phase was dried with anhydrous Na2SO4
  3. customevaporated
  4. customto remove organic solvents
  5. customThe obtained residue was further dried under high vacuum overnight
  6. customto give crude product, which
  7. customwas used directly for the next step synthesis without further purification

Sources & evidence

ORD record
ord-e06d24bf1aee4e20b2bd1c9a4c8bc5d3
Source dataset
uspto-grants-2015_06
Patent number
US09062023B2

Reaction notes

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