Triethylamine → HCID 60029922, compound

HRID 496449Notes

Reaction equation

HRID 496449 reaction equation
[N:1]1([CH2:6][C@@H:7]([O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:21](=[O:25])[CH2:20][CH2:19][CH2:18][C:17]=3[C:16]=2[CH2:26][S:27]([C:30]2[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=2[C:32]([OH:34])=O)(=[O:29])=[O:28])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:39](N1C=CN=C1)([N:41]1C=CN=C1)=O.C(N(CC)CC)C.Cl.CN>CN(C=O)C.O>[N:1]1([CH2:6][C@@H:7]([O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:21](=[O:25])[CH2:20][CH2:19][CH2:18][C:17]=3[C:16]=2[CH2:26][S:27]([C:30]2[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=2[C:32]([NH:41][CH3:39])=[O:34])(=[O:29])=[O:28])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 6364545Methylamine hydrochlorideHCID 20828716HCID 20828716, compound

Product 1

HCID 60029922HCID 60029922, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-{[(2-{[(1S)-2-(1H-imidazol-1-yl)-1-phenylethyl]oxy}-5-oxo-5,6,7,8-tetrahydro-1-naphthalenyl)methyl]sulfonyl}benzoic acid. (159 mg, 0.30 mmol) and 1,1′-carbonyldiimidazole (73 mg, 0.45 mmol) in DMF (2 ml) was stirred at 50° C.(bath) for 10 min. Triethylamine (0.21 ml, 1.50 mmol) and methylamine hydrochloride (61 mg, 0.90 mmol) were added. The reaction mixture was stirred at room temperature for 24 h. Water (15 ml) was added and stirred at 0° C. for 30 min. The precipitate was filtered, washed with water, and dried to give a crude product which was recrystalized from ethyl acetate-MeOH to afford the required compound as a light brown solid, 85 mg, 52% yield; mp 249-251° C. NMR was consistent with the structure. Calcd. For C30H29N3O5S:

Workup

  1. stirringstirred at 0° C. for 30 min
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customto give a crude product which
  6. customwas recrystalized from ethyl acetate-MeOH

Sources & evidence

ORD record
ord-0e94175ebce64ec6b0f86e49d7168cdb
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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