Water → HCID 68183339, compound

HRID 1615559Notes

Reaction equation

HRID 1615559 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:14]([C:15](O)=[O:16])[NH:13][C:12](=[O:18])[C:11]3[S:19][C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:21][C:10]2=3)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.C[N:30](C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[OH-].[NH4+].O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:14]([C:15]([NH2:30])=[O:16])[NH:13][C:12](=[O:18])[C:11]3[S:19][C:20]([N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)=[CH:21][C:10]2=3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 5

HCID 962WaterHCID 14923Ammonium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68183276HCID 68183276, compound

Product 1

HCID 68183339HCID 68183339, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of rel-(4R,5R)-4-(3,4-dichlorophenyl)-2-(morpholin-4-yl)-7-oxo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-5-carboxylic acid (0.100 g, 0.234 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.090 g, 0.47 mmol), 1-hydroxybenzotriazole hydrate (0.072 g, 0.47 mmol) in methylene chloride (4 mL) was added a solution of 33% ammonium hydroxide in water (0.40 mL, 4.7 mmol). The mixture was stirred at rt overnight. The mixture was concentrated and the residue was purified by silica gel chromatography. Final purification by HPLC afforded the product as a white solid. LCMS: (AA), ES+: 426, 428, 1H NMR (400 MHz, DMSO) δ 7.58 (d, J=8.3 Hz, 1H), 7.53-7.47 (m, 2H), 7.37 (d, J=4.2 Hz, 1H), 7.20 (s, 1H), 7.10 (dd, J=8.5, 2.0 Hz, 1H), 6.00 (s, 1H), 4.52 (s, 1H), 3.96 (dd, J=4.3, 2.2 Hz, 1H), 3.73-3.63 (m, 4H), 3.12 (d, J=5.6 Hz, 4H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by silica gel chromatography
  3. customFinal purification by HPLC

Sources & evidence

ORD record
ord-5c6e26cc3c9e4e21b6a6243b97192515
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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