Trifluoroacetic acid → HCID 178480076, compound

HRID 2174708Notes

Reaction equation

HRID 2174708 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[NH2:39][C@H:40]([CH2:56][CH2:57][C:58]1[NH:62][N:61]=[N:60][N:59]=1)[C:41]([NH:43][C:44]1[CH:55]=[CH:54][C:47]2[CH2:48][CH2:49][N:50]([CH3:53])[CH2:51][CH2:52][C:46]=2[CH:45]=1)=[O:42].C(O)(C(F)(F)F)=O>CN(C=O)C>[NH:62]1[C:58]([CH2:57][CH2:56][C@@H:40]([NH:39][C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:9])[C:41](=[O:42])[NH:43][C:44]2[CH:55]=[CH:54][C:47]3[CH2:48][CH2:49][N:50]([CH3:53])[CH2:51][CH2:52][C:46]=3[CH:45]=2)=[N:59][N:60]=[N:61]1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178480078HCID 178480078, compound

Product 1

HCID 178480076HCID 178480076, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

13 mg (0.08 mmol) 5-chloro-thiophene-2-carboxylic acid are dissolved in 0.5 ml DMF, mixed at room temperature with 26 mg (0.08 mmol) TBTU and 50 μl (0.45 mmol) NMM and stirred for 15 min. A solution of 32 mg (0.08 mmol) (R)-2-amino-N-(3-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-4-(1H-tetrazol-5-yl)-butyramide in 1 ml DMF is added to the reaction mixture and it is stirred overnight at room temperature. The reaction mixture is acidified with TFA, separated by chromatography through RP material (eluant: water/acetonitrile 95:5=>5:95) and then freeze-dried.

Workup

  1. stirringis stirred overnight at room temperature
  2. customseparated by chromatography through RP material (eluant: water/acetonitrile 95:5=>5:95)
  3. customfreeze-dried

Sources & evidence

ORD record
ord-893eb9c4e0944522b944f1c6ad36540b
Source dataset
uspto-grants-2015_06
Patent number
US09062034B2

Reaction notes

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