Triethylamine → HCID 68226432, compound

HRID 1952677Notes

Reaction equation

HRID 1952677 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([CH2:10][NH:11][C:12]([C:14]3[S:18][C:17]([C:19]([NH:21][C@@H:22]([CH2:26][NH:27][C:28]([C:30]4[S:31][CH:32]=[CH:33][CH:34]=4)=[O:29])[C:23]([OH:25])=[O:24])=[O:20])=[C:16]([CH3:35])[CH:15]=3)=[O:13])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.I[CH2:37][CH:38]([CH3:40])[CH3:39].C(N(CC)CC)C.CCOC(C)=O>CN(C=O)C>[CH2:37]([O:24][C:23](=[O:25])[C@@H:22]([NH:21][C:19]([C:17]1[S:18][C:14]([C:12](=[O:13])[NH:11][CH2:10][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH:3]=[N:2][NH:1]3)=[CH:15][C:16]=1[CH3:35])=[O:20])[CH2:26][NH:27][C:28]([C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)=[O:29])[CH:38]([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10556Isobutyl iodideHCID 68226874HCID 68226874, compound

Product 1

HCID 68226432HCID 68226432, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-2-({5-[(1H-Indazol-4-ylmethyl)-carbamoyl]-3-methyl-thiophene-2-carbonyl}-amino)-3-[(thiophene-2-carbonyl)-amino]-propionic acid (200 mg, 0.39 mmol), 1-Iodo-2-methylpropane (220 mg, 1.17 mmol), and triethylamine (0.16 ml, 1.17 mmol) in DMF (3 mL) was heated in a microwave at 100° C. for 30 min. The mixture was cooled to room temperature, treated with EtOAc (50 mL), washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by column (30-100% EtOAc in hexane) to give 0.1441 g (65%) white solid. MS m/e 567.9 (M+H+).

Workup

  1. washwashed with brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column (30-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-2e24ad91995e4627b584fd6f07b5059e
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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