Triethylamine → HCID 58550869, compound

HRID 2204253Notes

Reaction equation

HRID 2204253 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[O:12][CH3:13])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:38]1[N:46]2[C:41]([C:42]3([CH2:59][CH2:58][NH:57][CH2:56][CH2:55]3)[O:43][C:44]3[CH:50]=[C:49]([C:51]([O:53][CH3:54])=[O:52])[CH:48]=[CH:47][C:45]=32)=[CH:40][CH:39]=1.CCN(CC)CC>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:57]2[CH2:58][CH2:59][C:42]3([O:43][C:44]4[CH:50]=[C:49]([C:51]([O:53][CH3:54])=[O:52])[CH:48]=[CH:47][C:45]=4[N:46]4[CH:38]=[CH:39][CH:40]=[C:41]34)[CH2:55][CH2:56]2)=[O:9])=[CH:5][C:4]=1[O:12][CH3:13])[CH3:2]

Participants

7

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 299406594-Ethyl-3-methoxybenzoic acidHCID 58551707HCID 58551707, compound

Product 1

HCID 58550869HCID 58550869, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-ethyl-3-methoxy-benzoic acid (450 mg, 2.5 mmol), HATU (940 mg, 2.5 mmol), methyl spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-7′-carboxylate (830 mg, 2.5 mmol), and Et3N (1.7 mL, 9.9 mmol) in DMF (8 mL) was stirred at room temperature overnight. The reaction was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organics were dried over sodium sulfate, filtered and evaporated to yield a crude mixture that was purified by silica gel chromatography eluting with 0-30% EtOAc in hexanes to yield methyl 1′-(4-ethyl-3-methoxybenzoyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-7-carboxylate (1.1 g, quant). ESI-MS m/z calc. 460.5, found 461.5 (M+1)+; Retention time: 2.08 minutes (3 min run).

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto yield a crude mixture that
  6. customwas purified by silica gel chromatography
  7. washeluting with 0-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-9066f6b054a845f09297492fbe63fc94
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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