Triethylamine → N-(2,2-Dimethoxyethyl)-N-ethyl-3-(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanamide

HRID 446424Notes

Reaction equation

HRID 446424 reaction equation
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)[O:5]1)CC.[CH:19]([C:22]1[S:23][CH:24]=[C:25]([C:27]([N:29]2[CH2:34][C:33]3([CH2:39][CH2:38][N:37]([CH2:40][CH2:41][C:42]4[CH:55]=[CH:54][C:45]([CH2:46][CH2:47][O:48][CH2:49]CC(O)=O)=[CH:44][CH:43]=4)[CH2:36][CH2:35]3)[O:32][CH2:31][CH2:30]2)=[O:28])[N:26]=1)([CH3:21])[CH3:20].[CH2:56]([NH:58][CH2:59][CH:60]([O:63][CH3:64])[O:61][CH3:62])[CH3:57].C(N([CH2:70][CH3:71])CC)C>CN(C=O)C>[CH3:62][O:61][CH:60]([O:63][CH3:64])[CH2:59][N:58]([CH2:70][CH3:71])[C:56](=[O:5])[CH2:57][CH2:49][O:48][CH2:47][CH2:46][C:45]1[CH:54]=[CH:55][C:42]([CH2:41][CH2:40][N:37]2[CH2:38][CH2:39][C:33]3([O:32][CH2:31][CH2:30][N:29]([C:27]([C:25]4[N:26]=[C:22]([CH:19]([CH3:21])[CH3:20])[S:23][CH:24]=4)=[O:28])[CH2:34]3)[CH2:35][CH2:36]2)=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 3020444N-ethyl-2,2-dimethoxyethanamineHCID 462387963-(4-(2-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoic acid

Product 1

HCID 58168626N-(2,2-Dimethoxyethyl)-N-ethyl-3-(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

T3P (1.6M in THF, 0.33 mL) was added dropwise to a stirred solution of 3-(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoic acid [Example 1, step e] (0.3 g) and N-ethyl-2,2-dimethoxyethanamine [U.S. Pat. No. 2,707,186] (0.062 g) and triethylamine (0.46 mL) in DMF (7 mL). The reaction mixture was stirred at 20° C. for 3 hours. The mixture was partitioned between ethyl acetate and brine, the organic layer was washed with brine (×2), dried, filtered and the solvent evaporated under reduced pressure to yield the subtitled compound. Yield 0.26 g.

Workup

  1. customThe mixture was partitioned between ethyl acetate and brine
  2. washthe organic layer was washed with brine (×2)
  3. customdried
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-635369e516ee4151810a388372fe28aa
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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