Benzylethanolamine → 2-Chloro-N-[(1R,2R)-1-({[(2-hydroxyethyl)(phenylmethyl)amino]acetyl}amino)-2,3-dihydro-1H-inden-2-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1244718Notes

Reaction equation

HRID 1244718 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:12][C:13]1[S:37][C:16]2[NH:17][C:18]([C:20]([NH:22][C@@H:23]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C@H:24]3[NH:32][C:33](=[O:36])[CH2:34]Cl)=[O:21])=[CH:19][C:15]=2[CH:14]=1.CCN(CC)CC>C1COCC1>[Cl:12][C:13]1[S:37][C:16]2[NH:17][C:18]([C:20]([NH:22][C@@H:23]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C@H:24]3[NH:32][C:33](=[O:36])[CH2:34][N:8]([CH2:9][CH2:10][OH:11])[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:21])=[CH:19][C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 4348BenzylethanolamineHCID 8471TriethylamineHCID 587174892-Chloro-N-{(1R,2R)-1-[(chloroacetyl)amino]-2,3-dihydro-1H-inden-2-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

Product 1

HCID 103115922-Chloro-N-[(1R,2R)-1-({[(2-hydroxyethyl)(phenylmethyl)amino]acetyl}amino)-2,3-dihydro-1H-inden-2-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamideYield 36.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Benzylamino)ethanol (160 mg, 1.06 mmol) was added to a solution of 2-chloro-N-{(1R,2R)-1-[(chloroacetyl)amino]-2,3-dihydro-1H-inden-2-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 23; 216 mg, 0.53 mmol) and Et3N (500 μL, 3.60 mmol) in anhydrous THF (5 mL) and the reaction stirred for approximately 16 hours at room temperature then for a further 16 h at 50° C. The volatiles were removed under reduced pressure, the residue dissolved in EtOAc (10 mL), washed with H2O (2×10 mL) and dried (MgSO4). The solvent was removed under reduced pressure, the residue triturated (EtOAc:isohexane, 1:5), collected by filtration, washed with isohexane (10 mL) and dried to give the title compound (100 mg, 36%) as a brown solid.

Workup

  1. waitfor a further 16 h at 50° C
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe residue dissolved in EtOAc (10 mL)
  4. washwashed with H2O (2×10 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed under reduced pressure
  7. customthe residue triturated (EtOAc:isohexane, 1:5)
  8. filtrationcollected by filtration
  9. washwashed with isohexane (10 mL)
  10. customdried

Sources & evidence

ORD record
ord-bd1162ac1c7847059a72607d500acdae
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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