Benzofuran-2-carboxylic acid → HCID 45269797, compound

HRID 574309Notes

Reaction equation

HRID 574309 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]([CH2:21][CH2:22][CH3:23])[CH:10]2[CH2:19][CH2:18][C:17]3[C:16]([OH:20])=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:11]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[O:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH:26]=[C:25]1[C:33](O)=[O:34]>>[O:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH:26]=[C:25]1[C:33]([N:4]1[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][N:9]([CH:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[OH:20])[CH2:11]2)[CH2:21][CH2:22][CH3:23])[CH2:2][CH2:3]1)=[O:34]

Participants

3

Reactant 2

HCID 10331Benzofuran-2-carboxylic acidHCID 60167428HCID 60167428, compound

Product 1

HCID 45269797HCID 45269797, compoundYield 35%

Procedure

Compound 40h was prepared following Procedure G using 39b (214 mg, 0.674 mmol) and benzofuran-2-carboxylic acid (131 mg, 0.809 mmol) to give 40h (108 mg, 35%) after column chromatography. 1H NMR (400 MHz, CD3OD) δ 0.94-0.98 (t, 3H, J=7.2 Hz), 1.60-1.68 (m, 3H), 2.14-2.65 (m, 8H), 2.77-3.03 (m, 8H), 3.87 (bs, 4H), 6.55-6.60 (m 2H), 6.89-6.93 (t, 1H, J=7.2 Hz), 7.29-7.33 (t, 1H, J=6.4 Hz), 7.36 (s, 1H), 7.42-7.45 (t, 1H, J=7.2 Hz), 7.56-7.58 (d, 1H, J=8.8 Hz), 7.70-7.72 (d, 1H, J=7.2 Hz). The free base of 40h was converted in to its HCl salt. m.p. decomp at 140° C. Anal. [C28H35N3O.2HCl.1.5H2O] C, H, N.

Workup

  1. customCompound 40h was prepared

Sources & evidence

ORD record
ord-b0d5b85cae224aa5958cdd4f26ef570b
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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