5-Chloro-1H-indole-2-carboxylic acid → HCID 57143767, compound

HRID 1872144Notes

Reaction equation

HRID 1872144 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]([N:6]1[CH2:11][CH2:10][S:9][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>>[CH2:12]([C@H:3]([NH:2][C:29]([C:24]1[NH:25][C:26]2[C:22]([CH:23]=1)=[CH:21][C:20]([Cl:19])=[CH:28][CH:27]=2)=[O:30])[C:4](=[O:5])[N:6]1[CH2:11][CH2:10][S:9][CH2:8][CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 66548467HCID 66548467, compound

Product 1

HCID 57143767HCID 57143767, compound

Procedure

(S)-2-Amino-3-phenyl-1-thiomorpholin4-yl-propan-1-one hydrochloride (2.6 mmol) and 5-chloro-1H-indole-2-carboxylic acid (2.6 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, washed with acid first, then base). The crude product was then triturated with 1:1 ether-hexanes and dried. Yield 1.03 g, 94%; HPLC (60/40) 8.74 minutes (99%); PBMS 428/430 (MH+, 100%);

Workup

  1. custom0-25° C. reaction temperature
  2. washwashed with acid first
  3. customThe crude product was then triturated with 1:1 ether-hexanes
  4. customdried
  5. customHPLC (60/40) 8.74 minutes (99%)

Sources & evidence

ORD record
ord-7180ab1ecb304d899db11896b0f1d974
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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