4-Morpholineacetic acid → HCID 86703927, compound

HRID 1049929Notes

Reaction equation

HRID 1049929 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([OH:10])=O)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:35][C:36]1[CH:37]=[C:38]([C:43]2[CH:44]=[C:45]3[C:50](=[CH:51][CH:52]=2)[N:49]=[CH:48][N:47]=[C:46]3[NH2:53])[CH:39]=[C:40]([F:42])[CH:41]=1>C(Cl)Cl>[NH2:53][C:46]1[C:45]2[C:50](=[CH:51][CH:52]=[C:43]([C:38]3[CH:37]=[C:36]([NH:35][C:8](=[O:10])[CH2:7][N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)[CH:41]=[C:40]([F:42])[CH:39]=3)[CH:44]=2)[N:49]=[CH:48][N:47]=1

Participants

5

Reactant 3

HCID 4389684-Morpholineacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86703926HCID 86703926, compound

Product 1

HCID 86703927HCID 86703927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-morpholinoacetic acid (0.175 mmol, 25 mg) in a 4 mL vial was added HATU (0.175 mmol, 69 mg), 6-(3-amino-5-fluoro-phenyl)quinazolin-4-amine, 0.15 mmol, 38 mg), and TEA (0.30 mmol, 0.042 mL). The vial was capped and shaken overnight at room temperature. The reaction was then diluted with 3 mL DCM, then washed with 2 mL water. Organic phase was concentrated, and then purified by reverse phase HPLC yielding 20 mg of desired product. 1H NMR (400 MHz, DMSO) δ 10.07-9.93 (s, 1H), 8.60-8.52 (d, J=1.8 Hz, 1H), 8.42-8.39 (s, 1H), 8.08-8.03 (dd, J=8.7, 1.9 Hz, 1H), 7.93-7.66 (m, 4H), 7.44-7.35 (d, J=10.0 Hz, 1H), 3.71-3.63 (m, 4H), 3.20-3.17 (s, 2H), 2.56-2.51 (m, 4H). LCMS M/Z (M+H) 382.

Workup

  1. customThe vial was capped
  2. washwashed with 2 mL water
  3. concentrationOrganic phase was concentrated
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-9e90acee6aa4469d9bebf37f5026d110
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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