Ammonia → HCID 69779955, compound

HRID 1250403Notes

Reaction equation

HRID 1250403 reaction equation
[OH:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[N:29])[CH:23]=3)[C:12]3[C:17]([CH:18]=2)=[C:16]([O:19][CH3:20])[CH:15]=[CH:14][CH:13]=3)=[O:9])=[CH:4][CH:3]=1.[ClH:32].[NH3:33]>>[ClH:32].[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28](=[NH:33])[NH2:29])[CH:23]=3)[C:12]3[C:17]([CH:18]=2)=[C:16]([O:19][CH3:20])[CH:15]=[CH:14][CH:13]=3)=[O:9])=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 11144064HCID 11144064, compound

Product 1

HCID 69779955HCID 69779955, compoundYield 79%

Procedure

This compound was prepared from 1-(3-cyano-benzyl)-4-methoxy-1H-indole-2-carboxylic acid 4-hydroxy-benzyl amide (200 mg, 0.49 mmol), hydrogen chloride, and liquid ammonia analogously to example 19/3. Purification by reversed phase chromatography on RP18 material with water/ethanol/acetic acid 7:3:0.1 and lyophilization gave 179 mg of the desired product (79%). M.p. 202° C. (dec.). MS: 429.2 (100%; M+H+).

Workup

  1. customPurification by reversed phase chromatography on RP18 material with water/ethanol/acetic acid 7:3:0.1 and lyophilization

Sources & evidence

ORD record
ord-1aeec6dc36504537838c747ad85d633d
Source dataset
uspto-grants-2002_01
Patent number
US06337344B1

Reaction notes

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