4-Aminobenzonitrile → HCID 68818316, compound

HRID 735521Notes

Reaction equation

HRID 735521 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:21][C:22](=[O:35])[CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=2)[CH:13]=[CH:14][C:15]=1[S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:36][C:37]1[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][CH:38]=1.O.[C:46]([OH:50])(=[O:49])[CH:47]=O>>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:21][C:22](=[O:35])[CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([CH:47]([NH:36][C:37]3[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][CH:38]=3)[C:46]([OH:50])=[O:49])=[CH:28][CH:27]=2)[CH:13]=[CH:14][C:15]=1[S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 133964-AminobenzonitrileHCID 15620607Glyoxylic acid, monohydrateHCID 57842682HCID 57842682, compound

Product 1

HCID 68818316HCID 68818316, compound

Procedure

Using a procedure analogous to that used to prepare 2D, 15C (0.101 g, 0.20 mmol) was reacted with 4-aminobenzonitrile (0.024 g, 0.2 mmol) and glyoxylic acid monohydrate (0.018 g, 0.2 mmol) to give, after purification by reverse phase HPLC, 15D (78 mg, 62%) as a white solid. MS (ESI) m/z 634.9 (M+H)+.

Workup

  1. customto give
  2. customafter purification by reverse phase HPLC, 15D (78 mg, 62%) as a white solid

Sources & evidence

ORD record
ord-fd2ac2cf18894edc9cab7c4a656aa98d
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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