Benzo(b)thiophene-2-carboxylic acid → HCID 45267206, compound

HRID 574310Notes

Reaction equation

HRID 574310 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.[S:24]1[C:28]([C:29](O)=[O:30])=[CH:27][C:26]2[CH:32]=[CH:33][CH:34]=[CH:35][C:25]1=2>>[S:24]1[C:28]([C:29]([N:4]2[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][N:9]([CH:10]3[CH2:19][CH2:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][C:16]=4[OH:20])[CH2:11]3)[CH2:21][CH2:22][CH3:23])[CH2:2][CH2:3]2)=[O:30])=[CH:27][C:26]2[CH:32]=[CH:33][CH:34]=[CH:35][C:25]1=2

Participants

3

Reactant 2

HCID 95864Benzo(b)thiophene-2-carboxylic acidHCID 60167428HCID 60167428, compound

Product 1

HCID 45267206HCID 45267206, compoundYield 99.9%

Procedure

Compound 40i was prepared following Procedure G using 39b (175 mg, 0.551 mmol) and benzo[b]thiophene-2-carboxylic acid (118 mg, 0.661 mmol) to give 40i (263 mg, 64%) after column chromatography. 1H NMR (400 MHz, CD3OD) 0.91-0.97 (t, 3H, J=7.2 Hz), 1.53-1.68 (m, 3H), 2.50-2.63 (m, 7H), 2.78-3.02 (m, 7H), 3.77-3.79 (bs, 4H), 6.55-6.59 (t, 2H, J=8 Hz), 6.89-6.93 (t, 1H, J=8.4 Hz), 7.40-7.46 (m, 2H), 7.61 (s, 1H), 7.85-7.91 (m, 2H). The free base of 40i was converted into its HCl salt. m.p. 131-134° C. Anal. [C28H35N3O2S.2HCl.1.5H2O] C, H, N.

Workup

  1. customCompound 40i was prepared

Sources & evidence

ORD record
ord-ead88de655fe4d0a85071c38f67f0a28
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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