1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Chloro-N-(2-oxo-1,2,3,4-tetrahydro-1,7-naphthyridin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1178436Notes

Reaction equation

HRID 1178436 reaction equation
CC[N:3](C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:20][C:21]1[S:47][C:24]2[NH:25][C:26]([C:28]([NH:30][CH:31]3[CH2:40][C:39]4[C:34](=[CH:35]C=[CH:37][CH:38]=4)[N:33](CC(O)CO)[C:32]3=[O:46])=[O:29])=[CH:27][C:23]=2[CH:22]=1.ClC1SC2NC(C(NC3CC4C(=CC=CC=4)N(CC4ON=C(C)N=4)C3=O)=O)=CC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[Cl:20][C:21]1[S:47][C:24]2[NH:25][C:26]([C:28]([NH:30][CH:31]3[CH2:40][C:39]4[C:34](=[CH:35][N:3]=[CH:37][CH:38]=4)[NH:33][C:32]3=[O:46])=[O:29])=[CH:27][C:23]=2[CH:22]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 102527692-Chloro-N-[1-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamideHCID 117428502-chloro-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno(2,3-b)pyrrole-5-carboxamide

Product 1

HCID 219068482-Chloro-N-(2-oxo-1,2,3,4-tetrahydro-1,7-naphthyridin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamideYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (297 mg, 2.3 mmol), HOBT (128 mg, 0.95 mmol), 2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid (Method 9, 154 mg., 0.767 mmol) and 3-amino-3,4-dihydro-1,7-naphthyridin-2(1H)-one (Method 28, 300 mg, 0.767 mmol) were suspended in DCM (10 mL). EDCI (183 mg, 0.95 mmol) was then added and the reaction mixture stirred at ambient temperature for 2 hrs. The reaction mixture was filtered and the filtrate was diluted with ethyl acetate (100 mL), washed with saturated aqueous sodium bicarbonate (2×25 mL) and brine (25 mL), dried (MgSO4) and evaporated under reduced pressure to give a light brown solid which was washed with methanol (20 mL) and dried to give the title compound (45 mg, 17%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was diluted with ethyl acetate (100 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (2×25 mL) and brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give a light brown solid which
  7. washwas washed with methanol (20 mL)
  8. customdried

Sources & evidence

ORD record
ord-67444d95358e48628b8d5282ee5f78cb
Source dataset
uspto-grants-2007_10
Patent number
US07276517B2

Reaction notes

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