Oxalyl chloride → HCID 178457898, compound

HRID 1508024Notes

Reaction equation

C(O)(=O)C.[NH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[NH:19][CH:20]=[C:21]([C:23]#[N:24])[N:22]=2)=[O:17])=[C:11]([C:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=2)[CH:10]=1)([CH3:8])[CH3:7].[C:31](Cl)(=[O:35])[C:32](Cl)=[O:33].CC[N:39](C(C)C)C(C)C>>[C:23]([C:21]1[N:22]=[C:18]([C:16]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([C:6]([NH:5][C:31](=[O:35])[C:32]([NH2:39])=[O:33])([CH3:8])[CH3:7])=[CH:10][C:11]=2[C:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=2)=[O:17])[NH:19][CH:20]=1)#[N:24]

Participants

Reactant 3

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 178476304HCID 178476304, compound

Product 1

HCID 178457898HCID 178457898, compoundYield 34%

Procedure

The procedure of Example 4 was followed using 4-cyano-1H-imidazole-2-carboxylic acid [4-(1-amino-1-methyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide acetic acid salt (as prepared in Example 3, step (b), 28.0 mg, 0.0684 mmol), oxalyl chloride (51 μL, 0.10 mmol, 2.0 M in DCM) and DIEA (36 μL, 0.21 mmol). Flash chromatography on silica gel (1-2% MeOH/DCM) afforded 9.2 mg (34%) of the title compound as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.14 (d, 1H, J=8.4 Hz), 7.99 (s, 1H), 7.31 (dd, 1H, J=8.4, 2.3 Hz), 7.20 (d, 1H, J=2.3 Hz), 5.81 (m, 1H), 2.22-2.31 (m, 4H), 1.74-1.89 (m, 4H), 1.71 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C22H24N6O3, 421.2 (M+H). found 421.0.

Sources & evidence

ORD record: ord-55f6c538e2fe4787bcdab1a2132cad64
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221797B2

Reaction notes

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