Indole-2-carboxylic acid → HCID 44188280, compound

HRID 574307Notes

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)[CH:26]=[C:25]1[C:33](O)=[O:34]>>[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:25]3[NH:24][C:32]4[C:27]([CH:26]=3)=[CH:28][CH:29]=[CH:30][CH:31]=4)=[O:34])[CH2:3][CH2:2]1)[CH2:11]2

Participants

Reactant 2

HCID 72899Indole-2-carboxylic acid

HCID 60167428HCID 60167428, compound

Product 1

HCID 44188280HCID 44188280, compoundYield 62%

Procedure

Compound 40e was prepared following Procedure G using 39b (43 mg, 0.14 mmol) and indole-2-carboxylic acid (30 mg, 0.19 mmol) to give 40e (32 mg, 62%) after column chromatography. 1H NMR (400 MHz, CD3OD) δ 1.02-1.06 (t, 3H, J=7.2 Hz), 1.77-1.79 (m, 3H), 2.27 (m, 1H), 2.63-2.66 (bs, 4H), 3.03-3.16 (m, 5H), 3.30-3.41 (m, 3H), 3.89 (bs, 4H), 6.59-6.61 (d, 1H, J=7.6 Hz), 6.63-6.65 (d, 1H, J=8 Hz), 6.84 (s, 1H), 6.94-6.98 (t, 1H, J=7.2 Hz), 7.04-7.08 (t, 1H, J=7.2 Hz), 7.19-7.23 (t, 1H, J=7.2 Hz), 7.41-7.61 (d, 1H, J=8 Hz), 7.59-7.61 (d, 1H, J=8 Hz). The free base of 40e was then converted into its HCl salt. m.p. 166-165° C. Anal. [C28H36N4O2.3HCl] C, H, N.

Workup

customCompound 40e was prepared

Sources & evidence

ORD record: ord-a82a3621d7db4d22b67f5d5832543f96
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034877B2

Reaction notes

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