Ammonia → HCID 58109716, compound

HRID 2037456Notes

Reaction equation

HRID 2037456 reaction equation
[CH2:1]([C@@:4]1([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].N.C[N:31](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(Cl)Cl>CO.CCOC(C)=O.CN(C=O)C>[CH2:1]([C@@:4]1([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH2:31])=[O:18])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58109446HCID 58109446, compound

Product 1

HCID 58109716HCID 58109716, compoundYield 17.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-((S)-1-((R)-6-allyl-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)ethyl)benzoic acid (12 mg, 0.03 mmol), ammonia in methanol (c.a. 7N, 1 mL, excess), HATU (12 mg, 1.1 equiv.), and DIEPA (11 μL, 2 equiv.) were mixed in 4:1 CH2Cl2 and DMF (2 mL). The mixture was stirred overnight at rt, diluted with EtOAc (5 mL), washed with 5% aq HCl (2×2 mL). The organic layer was concentrated and purified by prep HPLC to afford 4-((S)-1-((R)-6-allyl-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)ethyl)benzamide (2 mg, 17.5%) product. LC-MS Method 1 tR=1.4 min, m/z=383 (M+1); 1H NMR (CDCl3) 7.55 (d, 2H), 7.25 (t, 2H), 7.03 (t, 2H), 6.94 (d, 2H), 6.03 (br d, 2H), 5.68 (m, 2H), 5.05 (dd, 2H), 2.95 (m, 1H), 1.54 (d, 3H).

Workup

  1. washwashed with 5% aq HCl (2×2 mL)
  2. concentrationThe organic layer was concentrated
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-59e06ba4f6e84b17a4531ad13b5399bf
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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