Triethylamine → HCID 68226885, compound

HRID 1952635Notes

Reaction equation

HRID 1952635 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:37])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:24](=[O:36])[NH:25][CH2:26][C:27]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:28]=2[CH:29]=[N:30][NH:31]3)=[CH:20][C:21]=1[CH2:22][CH3:23])=[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:79]1[CH:83]=[CH:82][CH:81]=[C:80]1[C:84](O)=[O:85]>CN(C=O)C.CCOC(C)=O>[CH3:8][O:9][C:10](=[O:37])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:24](=[O:36])[NH:25][CH2:26][C:27]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:28]=2[CH:29]=[N:30][NH:31]3)=[CH:20][C:21]=1[CH2:22][CH3:23])=[O:16])[CH2:12][NH:13][C:84]([C:80]1[S:79][CH:83]=[CH:82][CH:81]=1)=[O:85]

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 68226552HCID 68226552, compound

Product 1

HCID 68226885HCID 68226885, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-Amino-2-({3-ethyl-5-[(1H-indazol-4-ylmethyl)-carbamoyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester trifluoro-acetic acid salt (0.14 mmol) in anhydrous DMF (5 mL) was added triethylamine (0.06 ml, 0.42 mmol), HBTU (0.080 g, 0.21 mmol), HOBt (0.023 g, 0.17 mmol), and 2-Thiophenecarboxylic acid (0.022 g, 0.17 mmol). The mixture was stirred at room temperature 15 h, treated with EtOAc (30 mL), washed with brine, dried over sodium sulfate, filtered and evaporated. The solid residue was purified by column (30-100% EtOAc in hexane) to give 0.0280 g (37%) white foam. MS m/e 540.0 (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 (30-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-0b94ce7a55da42baa97c705ad068e82a
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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