Ammonium Chloride → HCID 58859804, compound

HRID 1785928Notes

Reaction equation

HRID 1785928 reaction equation
[C:1]([N:4]([C@H:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([C:26](=[O:35])[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C@@H:18]([CH3:36])[CH2:17]1)[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13](O)=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C([N:40](C1C2C(=CC=CC=2)N(C(=O)C2C=CC(OC)=CC=2)C(C)C1)C1C=CC(CCC(O)=O)=CC=1)(=O)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[NH4+].[Cl-].CCN(C(C)C)C(C)C>CN(C)C=O>[C:1]([N:4]([C@H:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([C:26](=[O:35])[C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[C@@H:18]([CH3:36])[CH2:17]1)[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([NH2:40])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 6

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21092867HCID 21092867, compoundHCID 57595437HCID 57595437, compound

Product 1

HCID 58859804HCID 58859804, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S,4R)-3-(4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenyl)-propionamide was prepared from (2S,4R)-3-(4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenyl)-propionic acid. To a solution of 3-(4-{acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenyl)-propionic acid (21 mg, 0.042 mmol) in dimethylformamide (200 μl) was added HATU (24 mg, 0.063 mmol), HOBt (8.5 mg, 0.063 mmol), NH4Cl (4.5 mg, 0.084 mmol) and DIPEA (29 μl, 0.168 mmol). Upon consumption of the starting unit (2.5 hours), the mixture was diluted with EtOAc (10 ml) and washed with sat. NaHCO3 (4X 10 ml). The EtOAc layer was collected, dried over Na2SO4, filtered, and concentrated to afford the title compound (17.2 mg, 82%).

Workup

  1. customUpon consumption of the starting unit (2.5 hours)
  2. additionthe mixture was diluted with EtOAc (10 ml)
  3. washwashed with sat. NaHCO3 (4X 10 ml)
  4. customThe EtOAc layer was collected
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-35c49c134b2142b981b72b68aabeb3d5
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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