Diisopropylethylamine → N-butyl-N-(2,2-dimethoxyethyl)-3-(2-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)phenethoxy)propanamide

HRID 446490Notes

Reaction equation

HRID 446490 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][O:26][CH:27]([O:34][CH3:35])[CH2:28][NH:29][CH2:30][CH2:31][CH2:32][CH3:33].[CH:36]([C:39]1[S:40][CH:41]=[C:42]([C:44]([N:46]2[CH2:51][C:50]3([CH2:56][CH2:55][N:54]([CH2:57][CH2:58][O:59][C:60]4[CH:73]=[CH:72][CH:71]=[CH:70][C:61]=4[CH2:62][CH2:63][O:64][CH2:65][CH2:66][C:67](O)=[O:68])[CH2:53][CH2:52]3)[O:49][CH2:48][CH2:47]2)=[O:45])[N:43]=1)([CH3:38])[CH3:37].CCN(C(C)C)C(C)C>CN(C)C=O>[CH2:30]([N:29]([CH2:28][CH:27]([O:26][CH3:25])[O:34][CH3:35])[C:67](=[O:68])[CH2:66][CH2:65][O:64][CH2:63][CH2:62][C:61]1[CH:70]=[CH:71][CH:72]=[CH:73][C:60]=1[O:59][CH2:58][CH2:57][N:54]1[CH2:53][CH2:52][C:50]2([O:49][CH2:48][CH2:47][N:46]([C:44]([C:42]3[N:43]=[C:39]([CH:36]([CH3:38])[CH3:37])[S:40][CH:41]=3)=[O:45])[CH2:51]2)[CH2:56][CH2:55]1)[CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21254099N-(2,2-dimethoxyethyl)butan-1-amineHCID 581685353-(2-(2-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)phenethoxy)propanoic acid

Product 1

HCID 58168462N-butyl-N-(2,2-dimethoxyethyl)-3-(2-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)phenethoxy)propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (0.337 g) was added to a stirred solution of N-(2,2-dimethoxyethyl)butan-1-amine (0.105 g), 3-(2-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-acid (0.390 g) (example 178 step d) and Hunig's Base (0.516 mL) in N,N-dimethylformamide (3 mL). After 1 h, the solution was partitioned between ethyl acetate and brine. The ethyl acetate layer was washed with brine (×3) and evaporated in vacuo. Purification was silica gel chromatography eluting with 10% triethylamine in ethyl acetate. Yield 0.4 g.

Workup

  1. customthe solution was partitioned between ethyl acetate and brine
  2. washThe ethyl acetate layer was washed with brine (×3)
  3. customevaporated in vacuo
  4. customPurification
  5. washeluting with 10% triethylamine in ethyl acetate

Sources & evidence

ORD record
ord-e14e98b120c34c2fb06c09832857c0b0
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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