Triethylamine → HCID 68226789, compound

HRID 1952657Notes

Reaction equation

HRID 1952657 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:31])[C@@H:5]([NH:8][C:9]([C:11]1[S:12][C:13]([C:18](=[O:30])[NH:19][CH2:20][C:21]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:22]=2[CH:23]=[N:24][NH:25]3)=[CH:14][C:15]=1[C:16]#[N:17])=[O:10])[CH2:6][NH2:7].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.C[O:74][C:75]1[CH:76]=[C:77]([CH:81]=[C:82]([O:84]C)[CH:83]=1)[C:78](O)=[O:79]>CN(C=O)C.CCOC(C)=O>[CH3:2][O:3][C:4](=[O:31])[C@@H:5]([NH:8][C:9]([C:11]1[S:12][C:13]([C:18](=[O:30])[NH:19][CH2:20][C:21]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:22]=2[CH:23]=[N:24][NH:25]3)=[CH:14][C:15]=1[C:16]#[N:17])=[O:10])[CH2:6][NH:7][C:78](=[O:79])[C:77]1[CH:76]=[C:75]([OH:74])[CH:83]=[C:82]([OH:84])[CH:81]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 143323,5-Dimethoxybenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68226677HCID 68226677, compound

Product 1

HCID 68226789HCID 68226789, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-Amino-2-({3-cyano-5-[(1H-indazol-4-ylmethyl)-carbamoyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester hydrochloride (0.40 mmol) in anhydrous DMF (10 mL) was added triethylamine (0.17 mL, 1.20 mmol), HBTU (0.18 g, 0.048 mmol), HOBt (0.065 g, 0.048 mmol), and 3,5-Dimethoxybenzoic acid (0.062 g, 0.40 mmol). The mixture was stirred at room temperature 1 h, treated with EtOAc (40 mL), washed with brine, dried over sodium sulfate, filtered and evaporated. The solid residue was purified by column (50-100% EtOAc in hexane) to give 0.1241 g (55%) colorless oil. MS m/e 563.0 (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 (50-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-baeea8a7f8bc4c8c9576a1ce90e7a175
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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