Triethylamine → HCID 68226476, compound

HRID 1952607Notes

Reaction equation

HRID 1952607 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:36])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:23](=[O:35])[NH:24][CH2:25][C:26]2[CH:34]=[CH:33][CH:32]=[C:31]3[C:27]=2[CH:28]=[N:29][NH:30]3)=[CH:20][C:21]=1[Cl:22])=[O:16])[CH2:12][NH2:13].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[S:78]1[CH:82]=[CH:81][CH:80]=[C:79]1[C:83](O)=[O:84]>CN(C=O)C.CCOC(C)=O>[CH3:8][O:9][C:10](=[O:36])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:23](=[O:35])[NH:24][CH2:25][C:26]2[CH:34]=[CH:33][CH:32]=[C:31]3[C:27]=2[CH:28]=[N:29][NH:30]3)=[CH:20][C:21]=1[Cl:22])=[O:16])[CH2:12][NH:13][C:83]([C:79]1[S:78][CH:82]=[CH:81][CH:80]=1)=[O:84]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 107002-Thiophenecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68226469HCID 68226469, compound

Product 1

HCID 68226476HCID 68226476, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-Amino-2-({3-chloro-5-[(1H-indazol-4-ylmethyl)-carbamoyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester trifluoro-acetic acid salt (0.19 mmol) in anhydrous DMF (5 mL) was added triethylamine (0.08 mL, 0.57 mmol), HBTU (0.108 g, 0.29 mmol), HOBt (0.031 g, 0.23 mmol), and 2-Thiophenecarboxylic acid (0.029 g, 0.23 mmol). The mixture was stirred at room temperature 2 h, treated with EtOAc (30 mL), washed with brine, dried over sodium sulfate, filtered and evaporated. The solid residue was purified by column (0-100% EtOAc in hexane) to give 0.0487 g (47%) colorless oil. MS m/e 545.9 (M+H+).

Workup

  1. washwashed with brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe solid residue was purified by column (0-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-8ffb765510b04d9895dea8368dfa82d4
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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