Methylamine → HCID 66631116, compound

HRID 2093533Notes

Reaction equation

HRID 2093533 reaction equation
[F:1][C:2]1[C:7]2[C:8]([C:18](O)=[O:19])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:21].CN.C1C=CC2N(O)N=[N:30][C:28]=2C=1.CCN=C=NCCCN(C)C.Cl.C(N(C(C)C)CC)(C)C>C1COCC1>[F:1][C:2]1[C:7]2[C:8]([C:18]([NH:30][CH3:28])=[O:19])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:21]

Participants

7

Reactant 5

HCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67979400HCID 67979400, compound

Product 1

HCID 66631116HCID 66631116, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4-fluoro-2-(4-bromophenyl)-5-hydroxybenzofuran-3-carboxylic acid (0.62 g, 1.77=10, 1 eq), 2M solution of methylamine in THF (5.4 ml, 10.8 mmol, 6.1 eq), HOBT (0.43 g, 3.18 mmol, 1.8 eq), EDCI.HCl (0.61 g, 3.18 mmol, 1.8 eq) in THF at r.t. under an nitrogen atmosphere was added diisopropylethylamine (1.9 ml, 10.9 mmol, 6.2 eq). The clear reaction mixture was stirred at r.t. overnight. The reaction mixture was concentrated and diluted with water, and then the solid precipitate was collected by filtration. The product was washed with petroleum ether and dried under vacuum. Yield: 0.51 g (79.7%). 1H NMR (400 MHz, DMSO-d6) δ 9.67 (s, 1H), 8.63 (t, J=4.4 Hz, 1H), 7.79-7.72 (m, 4H), 7.33 (d, J=8.8 Hz, 1H), 7.02 (m, 1H), 2.81 (d, J=4.4 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. filtrationthe solid precipitate was collected by filtration
  4. washThe product was washed with petroleum ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-613dfd00ce1f4bd88bcd98788851b438
Source dataset
uspto-grants-2013_05
Patent number
US08445497B2

Reaction notes

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