Tert-Butylamine → HCID 15295328, compound

HRID 2041174Notes

Reaction equation

HRID 2041174 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)#[N:2].[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:12]([NH:16][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 120874-Cyanobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 15295328HCID 15295328, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 4-cyanobenzoic acid (30 mg, 2.07 mmol), tert-butylamine (0.5 mL, 4.13 mmol), triethylamine (0.4 mL, 2.89 mmol), and HATU (1.1 g, 2.89 mmol) in anhydrous DMF (7 mL). Stir at ambient temperature for 17 h. Partition the reaction mixture between brine (15 mL) and diethyl ether (15 mL), separate the organic layer, dry over anhydrous Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with DCM to obtain the desired intermediate as a white solid (0.4 g, 89%). MS (ES+) m/z: 203 (M+H)+.

Workup

  1. customPartition the reaction mixture between brine (15 mL) and diethyl ether (15 mL)
  2. customseparate the organic layer
  3. dry with materialdry over anhydrous Na2SO4
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with DCM

Sources & evidence

ORD record
ord-a99f452e7dd345058e49ea88a2353596
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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