5-Chloro-1H-indole-2-carboxylic acid → HCID 178523869, compound

HRID 651134Notes

Reaction equation

HRID 651134 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1)[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)=[O:5].[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([C:29](O)=[O:30])=[CH:23]2>>[OH:12][CH:9]1[CH2:8][CH2:7][N:6]([C:4](=[O:5])[C@@H:3]([NH:2][C:29]([C:24]2[NH:25][C:26]3[C:22]([CH:23]=2)=[CH:21][C:20]([Cl:19])=[CH:28][CH:27]=3)=[O:30])[CH2:13][C:14]2[N:15]=[CH:16][NH:17][CH:18]=2)[CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 178479296HCID 178479296, compound

Product 1

HCID 178523869HCID 178523869, compound

Procedure

(S)-2-Amino-1-(4-hydroxy-piperidin-1-yl)-3-(1H-imidazol-4-yl)-propan-1-one hydrochloride (0.7 mmol) and 5-chloro-1H-indole-2-carboxylic acid (0.7 mmol) were coupled according to Procedure A (120 hour reaction time, acid wash omitted). The crude product was triturated twice with ether, with 1:1 ether-hexanes and the residue purified by chromatography on silica gel eluted with 5-20% ethanol in dichloromethane containing 0.5% ammonium hydroxide. Yield 232 mg, 81%; HPLC (40/60) 2.57 minutes (98%); PBMS 416/418 (MH+, 100%);

Workup

  1. customThe crude product was triturated twice with ether, with 1:1 ether-hexanes
  2. customthe residue purified by chromatography on silica gel
  3. washeluted with 5-20% ethanol in dichloromethane containing 0.5% ammonium hydroxide
  4. customHPLC (40/60) 2.57 minutes (98%)

Sources & evidence

ORD record
ord-bf6c6a6f40e142de9c8c6f6ccffa719f
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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