Indole-5-carboxaldehyde → HCID 45272332, compound

HRID 574304Notes

Reaction equation

HRID 574304 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]([CH2:21][CH2:22][CH3:23])[CH:10]2[CH2:19][C:18]3[CH:17]=[C:16]([OH:20])[CH:15]=[CH:14][C:13]=3[CH2:12][CH2:11]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[NH:24]1[C:32]2[C:27](=[CH:28][C:29]([CH:33]=O)=[CH:30][CH:31]=2)[CH:26]=[CH:25]1>>[NH:24]1[C:32]2[C:27](=[CH:28][C:29]([CH2:33][N:4]3[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][N:9]([CH2:21][CH2:22][CH3:23])[CH:10]4[CH2:19][C:18]5[CH:17]=[C:16]([OH:20])[CH:15]=[CH:14][C:13]=5[CH2:12][CH2:11]4)[CH2:2][CH2:3]3)=[CH:30][CH:31]=2)[CH:26]=[CH:25]1

Participants

3

Reactant 2

HCID 589040Indole-5-carboxaldehydeHCID 45139978HCID 45139978, compound

Product 1

HCID 45272332HCID 45272332, compoundYield 32.5%

Procedure

Compound 40b was prepared according to Procedure A using 39a (65 mg, 0.20 mmol) and indole-5-carboxaldehyde (35 mg, 0.24 mmol) to give 40b (29 mg, 32%) after column chromatography. 1H NMR (400 MHz, CDCl3) δ 0.84 (t, 3H, J=7.2 Hz), 1.33-1.44 (m, 3H), 1.85 (d, 1H, J=10.0 Hz), 2.41-2.82 (m, 19H), 3.60 (s, 2H), 6.35 (d, 1H, J=2.0 Hz), 6.49-6.58 (m, 2H), 6.85 (d, 1H, J=8.4 Hz), 7.14-7.20 (m, 2H), 7.31 (d, 1H, J=8.4 Hz), 7.54 (s, 1H), 8.38 (bs, 1H). The free base of 40b was converted into oxalate salt. m.p. 198-203° C. Anal. [C28H38N4O.2.5(COOH)2.3H2O]C, H, N.

Workup

  1. customCompound 40b was prepared

Sources & evidence

ORD record
ord-989945a79d9044489edf4a58e023b0e3
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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