Triethylamine → HCID 68226623, compound

HRID 1952622Notes

Reaction equation

HRID 1952622 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:38])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:25](=[O:37])[NH:26][CH2:27][C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[CH:30]=[N:31][NH:32]3)=[CH:20][C:21]=1[CH:22]([CH3:24])[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:80]1[CH:84]=[CH:83][CH:82]=[C:81]1[C:85](O)=[O:86]>CN(C=O)C.CCOC(C)=O>[CH3:8][O:9][C:10](=[O:38])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:25](=[O:37])[NH:26][CH2:27][C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[CH:30]=[N:31][NH:32]3)=[CH:20][C:21]=1[CH:22]([CH3:24])[CH3:23])=[O:16])[CH2:12][NH:13][C:85]([C:81]1[S:80][CH:84]=[CH:83][CH:82]=1)=[O:86]

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 68226562HCID 68226562, compound

Product 1

HCID 68226623HCID 68226623, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-Amino-2-({5-[(1H-indazol-4-ylmethyl)-carbamoyl]-3-isopropyl-thiophene-2-carbonyl}-amino)-propionic acid methyl ester trifluoro-acetic acid salt (0.33 mmol) in anhydrous DMF (8 mL) was added triethylamine (0.14 mL, 0.57 mmol), HBTU (0.188 g, 0.50 mmol), HOBt (0.054 g, 0.40 mmol), and 2-Thiophenecarboxylic acid (0.051 g, 0.40 mmol). The mixture was stirred at room temperature 15 h, treated with EtOAc (50 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 0.1096 g (60%) white foam. MS m/e 554.0 (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-4b7e4edf0a394c979dd01458e3a30731
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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