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Hexane → HCID 44243040, compound

HRID 1013091
Notes
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Reaction equation

HRID 1013091 reaction equation
CCCCCC.[CH2:7]([N:9]([Al](C)C)[CH2:10][CH3:11])[CH3:8].[CH2:15]([NH:17][C:18](=[O:49])[NH:19][C:20]1[S:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[C:21]=1[C:29]([N:31]1[CH2:48][CH2:47][C:34]2([N:38]=[C:37]([CH2:39][CH2:40][C:41]([O:43]CC)=O)[NH:36][C:35]2=[O:46])[CH2:33][CH2:32]1)=[O:30])[CH3:16]>C1C=CC=CC=1.C1COCC1>[CH2:7]([N:9]([CH2:10][CH3:11])[C:41](=[O:43])[CH2:40][CH2:39][C:37]1[NH:36][C:35](=[O:46])[C:34]2([CH2:33][CH2:32][N:31]([C:29]([C:21]3[C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=4[S:24][C:20]=3[NH:19][C:18]([NH:17][CH2:15][CH3:16])=[O:49])=[O:30])[CH2:48][CH2:47]2)[N:38]=1)[CH3:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8058HexaneHCID 16708834HCID 16708834, compoundHCID 44243038HCID 44243038, compound

Product 1

HCID 44243040HCID 44243040, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent
HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
80 °C

Procedure

To a 2.0 M hexane solution of (diethylamino)dimethylaluminum (3.2 equivalents) in dry benzene (0.26 M) was cooled to −15° C., a solution of ethyl 3-(8-(2-(3-ethylureido)benzo[b]thiophene-3-carbonyl)-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-2-yl)propanoate (10 (Example 10), 12 mg, 1.0 equivalent) in THF (0.16M) was added; the mixture was heated to 80° C. for 6 hrs. The mixture was cooled in an ice bath; then a saturated aqueous Rochelle's solution was added and stirred for 1 hr, then partitioned between ethyl acetate and water and the separated organics was washed with brine and dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by preparatory LCMS to afford N,N-diethyl-3-(8-(2-(3-ethylureido)benzo[b]thiophene-3-carbonyl)-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-2-yl)propanamide (10, 20%). Two rotamers observed (ratio 1.3:1).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. additionthen a saturated aqueous Rochelle's solution was added
  3. custompartitioned between ethyl acetate and water
  4. washthe separated organics was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparatory LCMS

Sources & evidence

ORD record
ord-1d3b65ccb6564805a438ed9d193f40e5
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981904B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes