Triethylamine → Benzo[b]thiophen-5-yl(9-(2-fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

HRID 1689375Notes

Reaction equation

HRID 1689375 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[S:25]1[CH:29]=[CH:28][C:27]2[CH:30]=[C:31]([C:34]([OH:36])=O)[CH:32]=[CH:33][C:26]1=2.[O:37]1[C:42]2([CH2:47][CH2:46][N:45]([CH2:48][C:49]3[C:50]([F:58])=[C:51]([CH2:55][CH2:56][OH:57])[CH:52]=[CH:53][CH:54]=3)[CH2:44][CH2:43]2)[CH2:41][NH:40][CH2:39][CH2:38]1.C(N(CC)CC)C>CN(C=O)C>[S:25]1[CH:29]=[CH:28][C:27]2[CH:30]=[C:31]([C:34]([N:40]3[CH2:41][C:42]4([CH2:47][CH2:46][N:45]([CH2:48][C:49]5[CH:54]=[CH:53][CH:52]=[C:51]([CH2:55][CH2:56][OH:57])[C:50]=5[F:58])[CH2:44][CH2:43]4)[O:37][CH2:38][CH2:39]3)=[O:36])[CH:32]=[CH:33][C:26]1=2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27954441-Benzothiophene-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 579891872-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-2-fluorophenyl)ethanol

Product 1

HCID 57988983Benzo[b]thiophen-5-yl(9-(2-fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (0.181 g) was added in one portion to a stirred solution at 0° C. of benzo[b]thiophene-5-carboxylic acid (0.065 g) and 2-(3-(1-oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-2-fluorophenyl)ethanol (example 67, step f) (0.113 g) and triethylamine (0.153 mL) in DMF (5 mL). The reaction mixture was stirred at room temperature for 2 hours. The mixture was partitioned between ethyl acetate and brine, the organic layer was washed twice with brine, dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 0.160 g.

Workup

  1. customThe mixture was partitioned between ethyl acetate and brine
  2. washthe organic layer was washed twice with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-646d31bb365f467aaa00012819d2a83a
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

Loading…