Tetrahydrofuran → HCID 178477880, compound

HRID 2415612Notes

Reaction equation

HRID 2415612 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C@H:13]3[CH2:18][CH2:17][C@@H:16]([NH2:19])[CH2:15][CH2:14]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH:20]([C:22]1[CH:30]=[C:29]2[C:25]([CH:26]=[CH:27][NH:28]2)=[CH:24][CH:23]=1)=O.C([BH3-])#N.O1CCCC1>C(O)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C@H:13]3[CH2:14][CH2:15][C@@H:16]([NH:19][CH2:20][C:22]4[CH:30]=[C:29]5[C:25]([CH:26]=[CH:27][NH:28]5)=[CH:24][CH:23]=4)[CH2:17][CH2:18]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 498716Cyano-borohydrideHCID 27734351H-Indole-6-carboxaldehydeHCID 178511631HCID 178511631, compound

Product 1

HCID 178477880HCID 178477880, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of example 23A (30 mg, 0.11 mmol), 6-formylindole (19.2 mg, 0.132 mmol) and solid supported cyanoborohydride (0.22 mmol) was shaken in 1:1 mixture tetrahydrofuran and acetic acid for 15 hours, filtered and concentrated. The residue was purified with a high throughput HPLC system to provide the desired compound as its bis TRIFLUOROACETIC ACID salt. MS (ESI(+)Q1MS m/z 405 (M+H)+); 1H NMR (300 MHz, DMSO-D6) δ ppm 11.31 (s, 1 H), 8.74 (d, 1 H), 8.49-8.79 (m, 2 H), 7.96 (d, 1 H), 7.85 (dd, 1 H), 7.62 (d, 1 H), 7.56 (s, 1 H), 7.45 (t, 1 H), 7.13 (d, 1 H), 6.94 (d, 1 H), 6.47 (t, 1 H), 4.28 (br.s, 1 H), 4.08 (br.s, 1 H), 2.27 (s, 2 H), 1.73-2.13 (m, 9 H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified with a high throughput HPLC system

Sources & evidence

ORD record
ord-c7ba6c65f5444e4ca9867dc7c0ed770e
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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