Indole-2-carboxylic acid → HCID 45271437, compound

HRID 574305Notes

Reaction equation

HRID 574305 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[C:33](O)=[O:34]>>[OH:20][C:16]1[CH:17]=[C:18]2[C:13]([CH2:12][CH2:11][CH:10]([N:9]([CH2:21][CH2:22][CH3:23])[CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][N:4]([C:33]([C:25]4[NH:24][C:32]5[C:27]([CH:26]=4)=[CH:28][CH:29]=[CH:30][CH:31]=5)=[O:34])[CH2:3][CH2:2]3)[CH2:19]2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 72899Indole-2-carboxylic acidHCID 45139978HCID 45139978, compound

Product 1

HCID 45271437HCID 45271437, compoundYield 86%

Procedure

Compound 40c was prepared following Procedure G using 39a (100 mg, 0.32 mmol) and indole-2-carboxylic acid (61 mg, 0.38 mmol) to give 40c (125 mg, 86%) after column chromatography. 1H NMR (400 MHz, CDCl3) δ 0.88 (t, 3H, J=7.2 Hz), 1.42-1.64 (m, 3H), 1.94 (brs, 1H), 2.51-2.75 (m, 14H), 2.88-2.96 (m, 1H), 3.95 (brs, 4H), 6.53 (brs, 1H), 6.59-6.61 (m, 1H), 6.75 (s, 1H), 6.90 (d, 1H, J=12.0 Hz), 7.11-7.18 (m, 1H), 7.22-7.26 (m, 1H), 7.40 (d, 1H, J=8.4 Hz), 7.62 (d, 1H, J=8.0 Hz), 9.72 (s, 1H). The free base of 40c was converted into HCl salt. m.p. 203-205° C. Anal. [C28H36N4O2.2HCl.1.2H2O] C, H, N.

Workup

  1. customCompound 40c was prepared

Sources & evidence

ORD record
ord-d44a882ff8164e318131375c8d975d77
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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