Ammonium Hydroxide → HCID 44156013, compound

HRID 572626Notes

Reaction equation

HRID 572626 reaction equation
[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)=[C:5]([C:14](O)=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].CC[N:27]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[OH-].[NH4+]>C(Cl)Cl>[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)=[C:5]([C:14]([NH2:27])=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2]

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 441558954-Cyano-3-(3,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid

Product 1

HCID 44156013HCID 44156013, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-cyano-3-(3,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid (0.198 g, 0.517 mmol) in DCM (5 mL) was added EDCI (0.198 g, 1.03 mmol) and HOBT (0.140 g, 1.03 mmol). The reaction mixture was stirred at rt for 30 min then ammonium hydroxide (1 mL, 20 mmol) was added. The reaction mixture was stirred for 4 h and was concentrated. The residue was diluted with water and extracted with EtOAc. The organic solutions were combined, washed with sat NaHCO3, with brine, dried over MgSO4, filtered and concentrated to give 4-cyano-3-(3,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxamide (84) (0.195 g, 99%). LCMS: (FA) ES+ 382.2, ES− 380.1. 1H NMR (300 MHz, d6-DMSO) δ: 7.73 (d, 1H), 7.64 (d, 1H), 7.36 (dd, 1H), 3.73-3.79 (m, 4H) and 3.49-3.54 (m, 4H).

Workup

  1. stirringThe reaction mixture was stirred for 4 h
  2. concentrationwas concentrated
  3. additionThe residue was diluted with water
  4. extractionextracted with EtOAc
  5. washwashed with sat NaHCO3, with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a33259c9ab4d4aa0bfe91b6ab5528722
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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