1,2-Dichloroethane → N,N-Diethyl-3-[7-(4-fluoro-benzyl)-9-hydroxy-5-methoxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-6-ylsulfanyl]-propionamide

HRID 853632Notes

Reaction equation

HRID 853632 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([OH:21])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:22][CH3:23])[C:9]=3[CH:8]2[S:24][CH2:25][CH2:26][C:27](O)=[O:28])=[CH:4][CH:3]=1.C(Cl)CCl.[CH2:36]([NH:38][CH2:39][CH3:40])[CH3:37]>C(Cl)Cl>[CH2:36]([N:38]([CH2:39][CH3:40])[C:27](=[O:28])[CH2:26][CH2:25][S:24][CH:8]1[C:9]2[C:10]([O:22][CH3:23])=[C:11]3[C:16](=[C:17]([OH:21])[C:18]=2[C:19](=[O:20])[N:7]1[CH2:6][C:5]1[CH:30]=[CH:31][C:2]([F:1])=[CH:3][CH:4]=1)[N:15]=[CH:14][CH:13]=[CH:12]3)[CH3:37]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 8021DiethylamineHCID 100034673-[[7-[(4-fluorophenyl)methyl]-9-hydroxy-5-methoxy-8-oxo-6H-pyrrolo[3,4-g]quinolin-6-yl]sulfanyl]propanoic acid

Product 1

HCID 10323596N,N-Diethyl-3-[7-(4-fluoro-benzyl)-9-hydroxy-5-methoxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-6-ylsulfanyl]-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 24 (10.7 mg, 0.024 mmol) in CH2Cl2 (0.24 mL) was stirred with EDC (14 mg, 0.73 mmol) and diethyl amine (10 μL, 0.097 mmol) for 1 day at ambient temperature. The product 25 was purified by reverse phase HPLC using 5-95% A. Buffer A contained CH3CN—1% HOAc and B contained H2O—1% HOAc. 1H NMR (300 MHz, CDCl3) δ 0.984 (t, 3H, J=6 Hz), 1.05 (t, 3H, J=7 Hz), 2.23-2.45 (m, 4H) 3.04 (q, 2H, J=7 Hz), 3.29 (q, 2H, J=8 Hz), 4.06 (s, 3H), 4.47 (d, 1H, J=14 Hz), 5.31 (d, 1H, J=15 Hz), 5.50 (s, 1H), 7.05 (t, 2H, J=9 Hz), 7.36-7.44 (m, 2H), 7.55-7.62 (m, 1H), J=9 Hz), 8.95-9.00 (m, 1H); EI MS (m/z) 520.2 [MH+], 1016.9 [2M+Na].

Workup

  1. customThe product 25 was purified by reverse phase

Sources & evidence

ORD record
ord-a5840553e3344296a64fc471130dc1b1
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

Loading…