Hydrochloric Acid → HCID 59843201, compound

HRID 2196497

Reaction equation

HRID 2196497 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:20])[C:10]([O:12]N1C(=O)CCC1=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26]1[N:30]([C:31]2[CH:32]=[C:33]([CH2:36][NH2:37])[S:34][CH:35]=2)[N:29]=[C:28]([C:38]([F:41])([F:40])[F:39])[CH:27]=1.CCN(CC)CC.Cl>C(Cl)Cl.CN(C=O)C>[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26]1[N:30]([C:31]2[CH:32]=[C:33]([CH2:36][NH:37][C:10](=[O:12])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:20])[S:34][CH:35]=2)[N:29]=[C:28]([C:38]([F:40])([F:41])[F:39])[CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11011585Boc-Ala-OSuHCID 59843286(4-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)methanamine

Product 1

HCID 59843201HCID 59843201, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

(S)-2,5-Dioxopyrrolidin-1-yl 2-(tert-butoxycarbonylamino)propanoate (130 mg, 0.45 mmol) was added to amine 5 (110 mg, 0.35 mmol) and Et3N (94.4 mg, 130 μL, 0.93 mmol) in DCM (2 mL) and DMF (0.2 mL) and the mixture was stirred at room temperature for 36 h. DCM was added followed by 1N HCl and the organic layer was separated and washed with H2O, then with saturated NaHCO3, dried over MgSO4, filtered and concentrated. The crude material was purified by chromatography (Biotage, 25+S column) eluting with 0-50% EtOAc/hexanes. Compound 6 was obtained in 49% yield as a white solid. LRMS (ESI): calc. 484.5; found 507.1 (MNa)+.

Workup

  1. customthe organic layer was separated
  2. washwashed with H2O
  3. dry with materialwith saturated NaHCO3, dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by chromatography (Biotage, 25+S column)
  7. washeluting with 0-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-7324f87f93a8403c9c040e9e6e16a035
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Linked notes

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