Indole-2-carboxaldehyde → HCID 45269785, compound

HRID 574306Notes

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][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1[CH:33]=O>>[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1[CH2:33][N:4]1[CH2:5][CH2:6][N: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)[CH2:2][CH2:3]1

Participants

Reactant 2

HCID 96389Indole-2-carboxaldehyde

HCID 45139978HCID 45139978, compound

Product 1

HCID 45269785HCID 45269785, compoundYield 87.5%

Procedure

Compound 40d was prepared according to Procedure A using 39a (100 mg, 0.32 mmol) and 1H-Indole-2-carbaldehyde (100 mg, 0.69 mmol) to give 40d (125 mg, 85%) after column chromatography. 1H NMR (400 MHz, CDCl3) δ 0.86 (t, 3H, J=7.2 Hz), 1.39-1.50 (m, 3H), 1.89 (brs, 1H), 2.41-2.73 (m, 18H), 2.82-2.88 (m, 1H), 3.65 (s, 2H), 6.35 (s, 1H), 6.44 (brs, 1H), 6.54-6.57 (m, 1H), 6.87 (d, 1H, J=8.8 Hz), 7.04-7.08 (m, 1H), 7.10-7.16 (m, 1H), 7.30 (d, 1H, J=7.6 Hz), 7.54 (d, 1H, J=8.0 Hz), 8.63 (s, 1H). The free base of 40d was converted into oxalate salt. m.p. 135-137° C. Anal. [C28H38N4O.3.0(COOH)2.0.3H2O] C, H, N.

Workup

customCompound 40d was prepared

Sources & evidence

ORD record: ord-477eddd3a81641b181811a006d2ca82f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034877B2

Reaction notes

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