Ammonium Hydroxide → HCID 68183031, compound

HRID 1615586Notes

Reaction equation

HRID 1615586 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][N:12]([CH2:14][C:15]([OH:17])=O)[C:11](=[O:18])[C:10]3[S:19][C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:21][C:9]2=3)=[CH:4][CH:3]=1.O.O[N:30]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH4+].[OH-]>CN(C=O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][N:12]([CH2:14][C:15]([NH2:30])=[O:17])[C:11](=[O:18])[C:10]3[S:19][C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:21][C:9]2=3)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 14923Ammonium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68182939HCID 68182939, compound

Product 1

HCID 68183031HCID 68183031, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-(4-chlorophenyl)-2-morpholino-7-oxo-4,5-dihydrothieno[2,3-c]pyridin-6(7H)-yl)acetic acid (95.2 mg, 0.234 mmol) in DMF (3.0 mL) was added 1-hydroxybenzotriazole hydrate (39.4 mg, 0.297 mmol) and N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (80.7 mg, 0.421 mmol) and the resulting solution was stirred for 30 minutes. 33% NH4OH (202 uL, 2.34 mmol) was added and the resulting solution was stirred at room temperature overnight. The reaction was diluted with ethyl acetate (40 mL) and water (15 mL). The layers were separated and the organic layer was washed with water (3×10 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give 77 mg crude. The residue was purified by analytical chromatography to give 50 mg (53% yield) of the title compound as a white solid. LC/MS (FA) ES+ 406. 1H NMR (400 MHz, DMSO-d6) δ: 7.42-7.39 (m, 2H), 7.28-7.26 (m and bs, 3H total), 7.01 (bs, 1H), 5.78 (s, 1H), 4.30-4.27 (m, 1H), 4.04 (d, 1H, J=17.2 Hz), 3.84-3.79 (m, 1H), 3.77 (d, 1H, J=17.2 Hz), 3.70-3.67 (m, 4H), 3.64-3.59 (m, 1H), 3.13-3.10 (m, 4H).

Workup

  1. stirringthe resulting solution was stirred at room temperature overnight
  2. customThe layers were separated
  3. washthe organic layer was washed with water (3×10 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give 77 mg crude
  8. customThe residue was purified by analytical chromatography

Sources & evidence

ORD record
ord-1614d75639f9467dbd1b2ec92a75ae43
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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