Hydrochloric Acid → Cyclopropane-1,1-dicarboxylic acid amide [2-fluoro-4-(4-fluoro-benzyloxy)-phenyl]-amide

HRID 1884148Notes

Reaction equation

HRID 1884148 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[NH2:17].Cl.[C:19]([C:22]1([C:25]([NH2:27])=[O:26])[CH2:24][CH2:23]1)(O)=[O:20].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>C(Cl)Cl.O>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[NH:17][C:19]([C:22]1([C:25]([NH2:27])=[O:26])[CH2:24][CH2:23]1)=[O:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27332721-(Aminocarbonyl)-1-cyclopropanecarboxylic acidHCID 221378852-Fluoro-4-(4-fluoro-benzyloxy)-phenylamine

Product 1

HCID 10382967Cyclopropane-1,1-dicarboxylic acid amide [2-fluoro-4-(4-fluoro-benzyloxy)-phenyl]-amideYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-fluoro-4-(4-fluoro-benzyloxy)-phenylamine (1:1) hydrochloride (272 mg, 1 mmol), 1-carboxycyclopropanecarboxamide (129 mg, 1 mmol), N-(3-dimethylaminopropyl)-N′ethylcarbodiimide hydrochloride (EDCI, 211 mg, 1.1 mmol) and triethylamine (111 mg, 1.1 mmol) in DCM (7 mL) was stirred at rt for 2 h. Then the mixture was poured into water and the mixture extracted with DCM. The combined organic extracts were then dried and evaporated to afford the title compound (130 mg, 38%) as a light brown solid after purification by chromatography on silica gel eluting with ethyl acetate: heptane (1:1 to 3:1). MS: m/e=347.0 (M++H).

Workup

  1. extractionthe mixture extracted with DCM
  2. customThe combined organic extracts were then dried
  3. customevaporated

Sources & evidence

ORD record
ord-9eb8f17fef6e48f98dcd591083ba8006
Source dataset
uspto-grants-2004_07
Patent number
US06762320B2

Reaction notes

Loading…