Diisopropylethylamine → HCID 57703899, compound

HRID 1472218Notes

Reaction equation

HRID 1472218 reaction equation
[NH2:1][C:2]1[CH:31]=[C:30]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)[CH:29]=[CH:28][C:3]=1[C:4]([NH:6][C:7]1[C:8]2[CH2:14][N:13]([S:15]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=3)(=[O:17])=[O:16])[C:12]([CH3:27])([CH3:26])[C:9]=2[NH:10][N:11]=1)=[O:5].C(N(CC)C(C)C)(C)C.C1C2C(COC([NH:65][C@@H:66]([CH3:70])[C:67](Cl)=[O:68])=O)C3C(=CC=CC=3)C=2C=CC=1>ClCCl>[NH2:65][C@@H:66]([CH3:70])[C:67]([NH:1][C:2]1[CH:31]=[C:30]([N:32]2[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]2)[CH:29]=[CH:28][C:3]=1[C:4]([NH:6][C:7]1[C:8]2[CH2:14][N:13]([S:15]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=3)(=[O:17])=[O:16])[C:12]([CH3:27])([CH3:26])[C:9]=2[NH:10][N:11]=1)=[O:5])=[O:68]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11142085Fmoc-Ala-ClHCID 57703910HCID 57703910, compound

Product 1

HCID 57703899HCID 57703899, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-N-[5-(3,5-difluoro-benzenesulfonyl)-6,6-dimethyl-1,4,5,6-tetrahydro-pyrrolo[3,4-c]pyrazol-3-yl]-4-(4-methyl-piperazin-1-yl)-benzamide (0.188 g, 0.34 mmol), N,N-diisopropylethylamine (0.59 mL, 3.4 mmol) and dichloromethane (10 mL), (S)-2-[(9H-fluoren-9-ylmethoxycarbonyl)amino]-propionyl chloride (0.448 g, 1.36 mmol, 4 eq.) was added and the reaction mixture stirred at room temperature overnight. After evaporation to dryness, the residue was treated with dichloromethane (10 mL), triethylamine (5 mL) and MeOH (5 mL) and the mixture stirred at room temperature for 72 hours. The solvent was then removed under vacuum and the residue purified by preparative HPLC/MS affording the title compound as white solid (0.105 g).

Workup

  1. customAfter evaporation to dryness
  2. additionthe residue was treated with dichloromethane (10 mL), triethylamine (5 mL) and MeOH (5 mL)
  3. stirringthe mixture stirred at room temperature for 72 hours
  4. customThe solvent was then removed under vacuum
  5. customthe residue purified by preparative HPLC/MS

Sources & evidence

ORD record
ord-086f851298ad426ebabe89b9051861ca
Source dataset
uspto-grants-2015_04
Patent number
US09012487B2

Reaction notes

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