2-Fluoroethylamine → HCID 86604700, compound

HRID 1867521Notes

Reaction equation

HRID 1867521 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]([NH:12][CH2:13][C:14]([OH:16])=O)=[O:11])[CH:8]=[CH:9][C:2]=12.[F:17][CH2:18][CH2:19][NH2:20].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[F:17][CH2:18][CH2:19][NH:20][C:14]([CH2:13][NH:12][C:10]([C:7]1[CH:8]=[CH:9][C:2]2[C:3]([CH:6]=1)=[N:4][O:5][N:1]=2)=[O:11])=[O:16]

Participants

7

Reactant 5

HCID 99962-FluoroethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14541744HCID 14541744, compound

Product 1

HCID 86604700HCID 86604700, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

221 mg (1 mmol) [(benzo[1,2,5]oxadiazole-5-carbonyl)-amino]-acetic acid, 120 mg (1.2 eq.) 2-fluoroethylamine, 162 mg (1.2 eq.) HOBt and 230 mg (1.2 eq.) EDC.HCl are dissolved in 18 mL DMF and cooled to 5° C. 0.7 mL (4 eq.) Hünig's base are added under stirring, the reaction mixture is stirred for an additional 3 hours at room temperature then extracted with water and ethyl acetate. The combined organic phases are washed with brine, dried with sodium sulfate and evaporated to yield the desired product as a beige solid. MS (ES+): 267 (M+1).

Workup

  1. stirringthe reaction mixture is stirred for an additional 3 hours at room temperature
  2. extractionthen extracted with water and ethyl acetate
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried with sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-c3b27929fed14c62ac7e3ce534d25ec5
Source dataset
uspto-grants-2009_12
Patent number
US07632851B2

Reaction notes

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