Triethylamine → HCID 71283715, compound

HRID 335296Notes

Reaction equation

HRID 335296 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[CH3:7][C:8]1([CH3:47])[CH2:12][CH2:11][CH2:10][N:9]1[CH2:13][CH2:14][NH:15][C:16]([C:18]1[CH:19]=[C:20]([NH:25][C:26]([C:28]2[CH:29]=[N:30][N:31]3[CH:36]=[C:35]([C:37]4[CH:45]=[CH:44][C:40]([C:41](O)=[O:42])=[C:39]([F:46])[CH:38]=4)[CH:34]=[CH:33][C:32]=23)=[O:27])[C:21]([CH3:24])=[N:22][CH:23]=1)=[O:17].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CN(C=O)C>[CH3:7][C:8]1([CH3:47])[CH2:12][CH2:11][CH2:10][N:9]1[CH2:13][CH2:14][NH:15][C:16]([C:18]1[CH:19]=[C:20]([NH:25][C:26]([C:28]2[CH:29]=[N:30][N:31]3[CH:36]=[C:35]([C:37]4[CH:45]=[CH:44][C:40]([C:41](=[O:42])[NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])=[C:39]([F:46])[CH:38]=4)[CH:34]=[CH:33][C:32]=23)=[O:27])[C:21]([CH3:24])=[N:22][CH:23]=1)=[O:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71283279HCID 71283279, compound

Product 1

HCID 71283715HCID 71283715, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-amino-2-methylpropan-1-ol (12.64 mg, 0.142 mmol), 4-(3-(5-(2-(2,2-dimethylpyrrolidin-1-yl)ethylcarbamoyl)-2-methylpyridin-3-ylcarbamoyl)pyrazolo[1,5-a]pyridin-6-yl)-2-fluorobenzoic acid (72 mg, 0.129 mmol) and triethylamine (0.054 ml, 0.387 mmol) in DCM (5 ml) was treated with HATU (53.9 mg, 0.142 mmol) and DMF (1 ml). After stirring at RT for 3 hrs, the reaction mixture was diluted with DCM and washed with sat NaHCO3 and H2O. The organic portion was separated, dried MgSO4 and concentrated in vacuo. The product was purified by flash column chromatography on silica eluting with 0-25% 2M NH3 in MeOH/DCM. The product fractions were combined and concentrated to afford an orange oil which was triturated with EtOAc/hexane to afford a pale brown solid.

Workup

  1. washwashed
  2. customThe organic portion was separated
  3. concentrationdried MgSO4 and concentrated in vacuo
  4. customThe product was purified by flash column chromatography on silica eluting with 0-25% 2M NH3 in MeOH/DCM
  5. concentrationconcentrated
  6. customto afford an orange oil which
  7. customwas triturated with EtOAc/hexane
  8. customto afford a pale brown solid

Sources & evidence

ORD record
ord-f96da884c2df4dfb8af308aef6e9de4b
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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