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Triethylamine → (2-Benzhydryl-5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)(5-methylthiophen-2-yl)methanone

HRID 1689272
Notes
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Reaction equation

HRID 1689272 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]1[S:30][C:29]([C:31]([OH:33])=O)=[CH:28][CH:27]=1.[CH:34]([N:47]1[CH2:50][C:49]2([CH2:55][NH:54][CH2:53][CH2:52][O:51]2)[CH2:48]1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(N(CC)CC)C>CN(C=O)C>[CH:34]([N:47]1[CH2:50][C:49]2([CH2:55][N:54]([C:31]([C:29]3[S:30][C:26]([CH3:25])=[CH:27][CH:28]=3)=[O:33])[CH2:53][CH2:52][O:51]2)[CH2:48]1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 747135-Methylthiophene-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579892372-(Diphenylmethyl)-5-oxa-2,8-diazaspiro[3.5]nonane

Product 1

HCID 57989184
(2-Benzhydryl-5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)(5-methylthiophen-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (2.267 g) was added in one portion to a solution of 5-methylthiophene-2-carboxylic acid (0.652 g) and 2-benzhydryl-5-oxa-2,8-diazaspiro[3.5]nonane (example 33, step f) (1.35 g) and triethylamine (1.917 mL) in DMF (20 mL) at 0° C. The cooling bath was removed and the mixture stirred at room temperature for 2 hours. The mixture was partitioned between ethyl acetate and brine, the organic layer was washed twice with brine before being dried over sodium sulphate, filtered and the solvent removed under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 0.4 to 5% methanol in dichloromethane. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 1.5 g.

Workup

  1. customThe cooling bath was removed
  2. customThe mixture was partitioned between ethyl acetate and brine
  3. washthe organic layer was washed twice with brine
  4. dry with materialbefore being dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe crude product was purified by flash silica chromatography, elution gradient 0.4 to 5% methanol in dichloromethane
  8. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-72042aee474e4b80868e70947ede23b5
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08148373B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes