Triethylamine → HCID 136252349, compound

HRID 710659Notes

Reaction equation

HRID 710659 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][NH:12][C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[NH:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[C:30]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[N:24]([CH2:31][C:32](O)=[O:33])[N:23]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:32](=[O:33])[CH2:31][N:24]4[C:25]5=[N:26][CH:27]=[CH:28][CH:29]=[C:30]5[C:22]([C:18]5[NH:17][CH:21]=[CH:20][N:19]=5)=[N:23]4)[C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridineHCID 1361746462-(3-(1H-imidazol-2-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)acetic acid

Product 1

HCID 136252349HCID 136252349, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine (0.050 g, 0.23 mmol), 2-[3-(1H-imidazol-2-yl)pyrazolo[3,4-b]pyridine-1-yl]acetic acid (0.050 g, 0.21 mmol) and Et3N (0.15 mL, 1.07 mmol) in DMF (0.7 mL) was added HATU (0.130 g, 0.33 mmol). The mixture was stirred at rt for 30 min. It was then quenched with water. The mixture was partitioned between IPA/CHCl3 (1:2, 100 mL) and sat. NaHCO3 (40 ml). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by reverse phase HPLC to afford the desired product (0.090 g, 96%). 1H NMR (TFA salt) (400 MHz, CD3OD) δ 8.73 (dd, J=4.8, 1.6 Hz, 1H), 8.69 (dd, J=8.0, 1.6 Hz, 1H), 8.14 (s, 1H), 7.72 (s, 2H), 7.55 (m, 3H), 7.28 (dd, J=9.2, 8.4 Hz, 2H), 5.89 (s, 2H), 4.06 (m, 2H), 2.92 (t, J=6.2 Hz, 2H), 2.20 (m, 2H); MS: (ES) m/z calculated for C23H19FN8O [M+H]+ 443.1, found 443.1.

Workup

  1. customIt was then quenched with water
  2. customThe mixture was partitioned between IPA/CHCl3 (1:2, 100 mL) and sat. NaHCO3 (40 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-3da858361e7e444aaed77616d6bd29e1
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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