Triethylamine → HCID 77846074, compound

HRID 595597Notes

Reaction equation

HRID 595597 reaction equation
[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37])=[CH:21][C:22]6[O:26][C:25]([C:27]([OH:29])=O)=[C:24]([C:30](=[O:33])[NH:31][CH3:32])[C:23]=6[CH:34]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1.C1C=CC2N(O)N=[N:47][C:45]=2C=1.CCN=C=NCCCN(C)C.Cl.CN.CCN(CC)CC>CN(C=O)C>[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:37])=[O:38])=[CH:21][C:22]6[O:26][C:25]([C:27]([NH:47][CH3:45])=[O:29])=[C:24]([C:30]([NH:31][CH3:32])=[O:33])[C:23]=6[CH:34]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 90333956HCID 90333956, compound

Product 1

HCID 77846074HCID 77846074, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylic acid (50 mg, 0.09 mmol), HOBT (24 mg, 0.17 mmol), EDCI (102 mg, 0.53 mmol), methanamine hydrochloride (42 mg, 0.62 mmol) and Et3N (72 mg, 0.71 mmol) in DMF (2 mL) was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, the residue was purified by prep-TLC (DCM:MeOH=200:1) to give the product 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-N2,N3-dimethyl-6-(N-methylmethylsulfonamido)benzofuran-2,3-dicarboxamide (20 mg, yield: 39%). 1H NMR (CDCl3, 400 MHz) δ 10.49 (br s, 1H), 8.81 (s, 1H), 7.68 (s, 1H), 7.49 (s, 2H), 7.24˜7.17 (m, 3H), 7.12 (d, J=8.2 Hz, 1H), 6.88˜6.81 (m, 1H), 6.01 (s, 2H), 3.39 (s, 3H), 3.12 (d, J=5.2 Hz, 3H), 3.02 (d, J=4.8 Hz, 3H), 2.65 (s, 3H). MS (M+H)+: 578.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by prep-TLC (DCM:MeOH=200:1)

Sources & evidence

ORD record
ord-2fafe1cef7784316b18dd05f86536582
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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