Indole-3-Carboxylic Acid → HCID 45273217, compound

HRID 574308Notes

Reaction equation

HRID 574308 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.[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([C:33](O)=[O:34])=[CH:25]1>>[OH:20][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[CH2:18][CH2:19][CH:10]([N:9]([CH2:21][CH2:22][CH3:23])[CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][N:4]([C:33]([C:26]3[C:27]4[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=4)[NH:24][CH:25]=3)=[O:34])[CH2:3][CH2:2]1)[CH2:11]2

Participants

3

Reactant 2

HCID 69867Indole-3-Carboxylic AcidHCID 60167428HCID 60167428, compound

Product 1

HCID 45273217HCID 45273217, compoundYield 53%

Procedure

Compound 10f was prepared following Procedure G using 39b (50 mg, 0.16 mmol) and indole-3-carboxylic acid (35 mg, 0.21 mmol) to give 40f (38 mg, 53%) after column chromatography. 1H NMR (400 MHz, CD3OD) δ 1.03-1.07 (t, 3H, J=7.2 Hz), 1.83-1.96 (m, 3H), 2.32 (s, 1H), 2.53-2.67 (m, 5H), 2.81-2.83 (m, 2H), 3.09-3.18 (m, 4H), 3.41-3.47 (m, 2H), 3.56-3.59 (m, 1H), 3.79 (bs, 4H), 6.61-6.63 (d, 1H, J=8.4 Hz), 6.64-6.66 (d, 1H, J=8.4 Hz), 6.96-6.99 (t, 1H, J=7.2 Hz), 7.13-7.21 (m, 1H), 7.41-7.51 (m, 1H), 7.62-7.64 (m, 1H), 7.71-7.73 (d, 1H, J=7.2 Hz), 7.83-7.84 (1H, J=7.2 Hz). The free base of 40f was converted into its HCl salt. m.p. 147-151° C. Anal. [C28H36N4O2.3HCl] C, H, N.

Sources & evidence

ORD record
ord-ddf21622712047778716b3f9e8b7b434
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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