Triethylamine → HCID 131730329, compound

HRID 1948321Notes

Reaction equation

HRID 1948321 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[C:30]([Cl:31])=[C:29]([CH3:32])[NH:28][C:27]=1[C:33]([NH:35][C@H:36]1[CH2:41][CH2:40][N:39]([C:42]2[CH:50]=[C:49]([C:51]([O:53][CH2:54][CH3:55])=[O:52])[C:45]([C:46]([OH:48])=O)=[CH:44][N:43]=2)[CH2:38][C@H:37]1[O:56][CH3:57])=[O:34].CCN(CC)CC.[C:65]([NH2:74])([C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1)([CH3:67])[CH3:66]>CN(C=O)C.O>[Cl:25][C:26]1[C:30]([Cl:31])=[C:29]([CH3:32])[NH:28][C:27]=1[C:33]([NH:35][C@H:36]1[CH2:41][CH2:40][N:39]([C:42]2[CH:50]=[C:49]([C:45]([C:46]([NH:74][C:65]([CH3:67])([C:68]3[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=3)[CH3:66])=[O:48])=[CH:44][N:43]=2)[C:51]([O:53][CH2:54][CH3:55])=[O:52])[CH2:38][C@H:37]1[O:56][CH3:57])=[O:34]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 68509CumylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131730327HCID 131730327, compound

Product 1

HCID 131730329HCID 131730329, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HATU (87 mg, 24 mmol) was added to a solution of 118 mg (0.24 mmol) Cis(±)-6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-(ethoxycarbonyl)nicotinic acid (Example 197), 0.040 ml (28 mmol) Et3N and 33 mg (0.24 mmol) cumylamine in 3 ml DMF. After stirring at room temperature overnight, the mixture was diluted with water and extracted with EtOAc. The EtOAc was washed 2 times with water and once with brine before being dried (MgSO4) and concentrated to give 103 mg of a solid. MS (ES) MH+: 616 for C30H35Cl2N5O5.

Workup

  1. extractionextracted with EtOAc
  2. washThe EtOAc was washed 2 times with water
  3. dry with materialonce with brine before being dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cc8b1166ab7c4d47a81975c389a339db
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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