Triethylamine → 2-Methylpentane

HRID 1689323Notes

Reaction equation

HRID 1689323 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:27][C:28]2[CH:34]=[CH:33][C:32]([C:35]([OH:37])=O)=[CH:31][C:29]=2[N:30]=1.[Si:38]([O:45][CH2:46][CH2:47][C:48]1[CH:49]=[C:50]([CH2:53][N:54]2[CH2:64][CH2:63][C:57]3([O:62][CH2:61][CH2:60][NH:59][CH2:58]3)[CH2:56][CH2:55]2)[S:51][CH:52]=1)([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39].C(N(CC)CC)C>CN(C=O)C>[CH3:28][CH2:29][CH2:31][CH:32]([CH3:35])[CH3:33].[Si:38]([O:45][CH2:46][CH2:47][C:48]1[CH:49]=[C:50]([CH2:53][N:54]2[CH2:64][CH2:63][C:57]3([O:62][CH2:61][CH2:60][N:59]([C:35]([C:32]4[CH:33]=[CH:34][C:28]5[S:27][C:26]([CH3:25])=[N:30][C:29]=5[CH:31]=4)=[O:37])[CH2:58]3)[CH2:56][CH2:55]2)[S:51][CH:52]=1)([C:41]([CH3:42])([CH3:43])[CH3:44])([CH3:40])[CH3:39]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 6499532-Methyl-1,3-benzothiazole-5-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579891139-((4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecane

Product 2

HCID 78922-MethylpentaneHCID 57989353(9-((4-(2-(Tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylbenzo[d]thiazol-5-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (0.333 g) was added to stirred solution of 2-methylbenzo[d]thiazole-5-carboxylic acid (0.17 g), 9-((4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecane (example 43, step b) (0.3 g) and triethylamine (0.407 mL) in DMF (3 mL). After 1 h, the reaction mixture was partitioned between water and ethyl acetate. The ethyl acetate layer was washed twice with water, once with brine, dried over magnesium sulphate, filtered and evaporated in vacuo. Purification by silica gel chromatography eluting with ethyl acetate:isohexane:triethylamine, 2:8:1 gave the subtitled compound as a gum. Yield 0.36 g.

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. washThe ethyl acetate layer was washed twice with water, once with brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by silica gel chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-95fcf5b6ac0043e7b5e297c4bacfc62b
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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