Triethylamine → HCID 72703925, compound

HRID 1049927Notes

Reaction equation

HRID 1049927 reaction equation
Cl.Cl.Cl.[NH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[CH:12]=[CH:13][C:14]3[N:15]=[CH:16][N:17]=[C:18]([NH2:21])[C:19]=3[N:20]=2)[CH2:6]1.[CH3:22][O:23][CH2:24][CH2:25][C:26](O)=[O:27].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O>[NH2:21][C:18]1[C:19]2[N:20]=[C:11]([N:7]3[CH2:8][CH2:9][CH2:10][C@H:5]([NH:4][C:26](=[O:27])[CH2:25][CH2:24][O:23][CH3:22])[CH2:6]3)[CH:12]=[CH:13][C:14]=2[N:15]=[CH:16][N:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1344423-Methoxypropionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86703924HCID 86703924, compound

Product 1

HCID 72703925HCID 72703925, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To an 8 mL screw-cap vial was added (S)-6-(3-aminopiperidin-1-yl)pyrido[3,2-d]pyrimidin-4-amine trihydrochloride 44 (0.15 mmol, 53 mg) followed by 3-methoxypropanoic acid (1.2 equiv., 0.18 mmol, 19 mg), HATU (1.2 equiv., 0.18 mmol, 68 mg), dimethylformamide (1 mL), then triethylamine (6 equiv., 0.90 mmol, 0.13 mL). The reaction was capped and shaken at room temperature overnight. The reaction was diluted with 3 mL DCM, and washed with 2 mL water. Organic was concentrated via GeneVac, then purified by reverse phase HPLC, yielding 15 mg of desired product. 1H NMR (400 MHz, DMSO) δ 8.19-8.14 (s, 1H), 7.91-7.83 (d, J=7.0 Hz, 1H), 7.82-7.73 (d, J=9.3 Hz, 1H), 7.44-7.38 (d, J=9.3 Hz, 1H), 7.38-7.18 (m, 2H), 4.25-4.17 (d, J=12.7 Hz, 1H), 4.17-4.08 (d, J=13.8 Hz, 1H), 3.85-3.72 (m, 1H), 3.58-3.48 (m, 2H), 3.23-3.18 (s, 3H), 3.10-2.99 (m, 1H), 2.37-2.28 (m, 2H), 1.90-1.81 (m, 1H), 1.81-1.70 (m, J=8.7 Hz, 1H), 1.63-1.40 (m, 2H). LCMS M/Z (M+H)=331.

Workup

  1. customTo an 8 mL screw-cap vial
  2. customThe reaction was capped
  3. washwashed with 2 mL water
  4. concentrationOrganic was concentrated via GeneVac
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-242c1dd2809e40ffa0e7dbea921673da
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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