Isopropylamine → HCID 58081221, compound

HRID 928409Notes

Reaction equation

HRID 928409 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([OH:20])=O)=[CH:14][CH:13]=2)[CH:10]=1)=[O:5])[CH3:2].CC[N:23](C(C)C)[CH:24]([CH3:26])[CH3:25].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)(C)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18](=[O:20])[NH:23][CH:24]([CH3:26])[CH3:25])=[CH:16][CH:17]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58081217HCID 58081217, compound

Product 1

HCID 58081221HCID 58081221, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 1-(4-carboxy-benzyl)-1H-pyrazole-4-carboxylic acid ethyl ester (50 mg, 0.153 mmol) in DCM (1 ml) were added DIPEA (40.1 μl, 0.230 mmol), HBTU (63.9 mg, 0.168 mmol) and isopropylamine (13 μl, 0.153 mmol). Reaction mixture was stirred over a weekend at 23° C. The solvent was evaporated, and the residual oil was dissolved in ethyl acetate and washed with 1M hydrochloric acid, saturated sodium bicarbonate solution and brine. Organic layer was dried (sodium sulfate), filtered and evaporated to afford the title compound. HPLC (method G) Rt=1.761 min; UPLC (method F) Rt=0.79 min, MS [M+H]+316.3.

Workup

  1. customReaction mixture
  2. customThe solvent was evaporated
  3. dissolutionthe residual oil was dissolved in ethyl acetate
  4. washwashed with 1M hydrochloric acid, saturated sodium bicarbonate solution and brine
  5. dry with materialOrganic layer was dried (sodium sulfate)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a2b42e2945e84753a4c28c979abb5529
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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