Dimethylformamide → HCID 52946059, compound

HRID 1519987Notes

Reaction equation

HRID 1519987 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N:15]1([C:20]2[S:21][CH:22]=[CH:23][C:24]=2[NH2:25])[CH:19]=[CH:18][N:17]=[CH:16]1.CN1CCOCC1.CN(C=O)C>C(Cl)Cl>[N:15]1([C:20]2[S:21][CH:22]=[CH:23][C:24]=2[NH:25][C:12](=[O:14])[CH2:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 68621-Naphthaleneacetic AcidHCID 79724-MethylmorpholineHCID 20823829HCID 20823829, compound

Product 1

HCID 52946059HCID 52946059, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-naphthyl acetic acid and 2-(1H-imidazol-1-yl)thiophen-3-amine in anhydrous CH2Cl2 was added O-(7-azabenzotriazol-1-yl)-N,N,N,N,-tetramethyl uronium hexafluorophosphate and 4-methymorpholine. A small amount of DMF was added to help starting material reagents go into solution. The reaction mixture was stirred overnight under N2 (g) inlet and evaporated under reduced pressure. The resulting residue was purified by flash column chromatography (silica, 10:90 methanol/methylene chloride) to afford N-(2-(1H-imidazol-1-yl)thiophen-3-yl)2-(naphthalen-1-yl)acetamide (209 mg, 33%). The desired product was purified by preparative HPLC. Method [8] m/z 334.1 (M+H); retention time=4.885. 1H-NMR (CD3OD) δ 8.83 (s, 1H), 7.89-7.80 (m, 2H), 7.77 (d, J=7.8 Hz, 1H), 7.51 (d, J=6.3 Hz, 2H), 7.48-7.32 (m, 5H), 7.17 (d, J=6.3 Hz, 2H), 4.08 (s, 2H).

Workup

  1. customevaporated under reduced pressure
  2. customThe resulting residue was purified by flash column chromatography (silica, 10:90 methanol/methylene chloride)

Sources & evidence

ORD record
ord-3399f6e82dff4bbaa8c2a4762ce69737
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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