HCl tetrahydrofuran → HCID 178424500, compound

HRID 1508159Notes

Reaction equation

HRID 1508159 reaction equation
[CH3:1][C:2]1([CH3:38])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([CH3:27])([CH3:26])[CH2:15][N:16]3[CH2:20][CH:19]4[O:21]C(C)(C)[O:23][CH:18]4[CH2:17]3)[CH:11]=[CH:10][C:9]=2[NH:28][C:29]([C:31]2[NH:32][CH:33]=[C:34]([C:36]#[N:37])[N:35]=2)=[O:30])=[CH:4][CH2:3]1.[ClH:39].C1COCC1>CCOC(C)=O>[ClH:39].[OH:21][CH:19]1[CH:18]([OH:23])[CH2:17][N:16]([CH2:15][C:14]([C:12]2[CH:11]=[CH:10][C:9]([NH:28][C:29]([C:31]3[NH:32][CH:33]=[C:34]([C:36]#[N:37])[N:35]=3)=[O:30])=[C:8]([C:5]3[CH2:6][CH2:7][C:2]([CH3:38])([CH3:1])[CH2:3][CH:4]=3)[CH:13]=2)([CH3:27])[CH3:26])[CH2:20]1

Participants

4

Reactant 2

HCID 18422008HCl tetrahydrofuranHCID 178424499HCID 178424499, compound

Product 1

HCID 178424500HCID 178424500, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-cyano-1H-imidazole-2-carboxylic acid {2-(4,4-dimethyl-cyclohex-1-enyl)-4-[2-(2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-1,1-dimethyl-ethyl]-phenyl}-amide (as prepared in Example 140, 42.0 mg, 0.0811 mmol) in 2 mL of 1:1 1N HCl/THF was stirred at 80° C. for 0.5 h. After cooling to RT, the mixture was treated with 40 mL of EtOAc and concentrated in vacuo to give the title compound (38.8 mg, 91%) as a colorless oil. 1H-NMR (1:1 CD3OD; 400 MHz): 8.29 (d, 1H, J=8.6 Hz), 8.00 (s, 1H), 7.43 (dd, 1H, J=8.6, 2.3 Hz), 7.32 (d, 1H, J=2.3 Hz), 5.77 (m, 1H), 4.17 (m, 2H), 3.64 (s, 2H), 3.31-3.37 (m, 2H), 2.98-3.07 (m, 2H), 2.34 (m, 2H), 2.09 (m, 2H), 1.61 (t, 2H, J=6.3 Hz), 1.51 (s, 6H), 1.10 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C27H35N5O3, 478.3 (M+H). found 478.3.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8451b6619de14582a07ace28cd2043d2
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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