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Triethylamine → HCID 58551319, compound

HRID 1907980
Notes
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Reaction equation

HRID 1907980 reaction equation
[NH4+].[Cl-].CC[N:5](CC)CC.[C:10]([O:14][C:15]([N:17]1[CH2:37][CH2:36][C:20]2([C:25]3=[CH:26][CH:27]=[CH:28][N:24]3[C:23]3[CH:29]=[CH:30][C:31]([C:33]([OH:35])=O)=[CH:32][C:22]=3[O:21]2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[C:33]([C:31]1[CH:30]=[CH:29][C:23]2[N:24]3[CH:28]=[CH:27][CH:26]=[C:25]3[C:20]3([CH2:19][CH2:18][N:17]([C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[CH2:37][CH2:36]3)[O:21][C:22]=2[CH:32]=1)(=[O:35])[NH2:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 25517Ammonium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58550886HCID 58550886, compound

Product 1

HCID 58551319HCID 58551319, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of NH4Cl (1.4 mL, 40 mmol) and Et3N (5.6 mL, 40 mmol) in DMF (6 mL) was added to a solution of 1-tert-butoxycarbonylspiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-7′-carboxylic acid (3.1 g, 8.0 mmol), HATU (3.3 g, 8.8 mmol), and Et3N (2.5 mL, 18 mmol) in DMF (6 mL). The mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate and was washed with saturated sodium bicarbonate solution. The organics were dried over sodium sulfate, filtered and evaporated. Purification of the residue by silica gel chromatography eluting with 0-100% EtOAc in Hexanes gave tert-butyl 7′-carbamoylspiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (2.7 g, 89%). ESI-MS m/z calc. 383.4. found 384.7 (M+1)+. Retention time: 1.60 minutes (3 min run).

Workup

  1. washwas washed with saturated sodium bicarbonate solution
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customPurification of the residue by silica gel chromatography
  6. washeluting with 0-100% EtOAc in Hexanes

Sources & evidence

ORD record
ord-87168021526849329ce41c0d64f65e2c
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08598164B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes