Diisopropylethylamine → HCID 86609179, compound

HRID 1711296Notes

Reaction equation

[CH3:1][N:2]([CH3:25])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([C:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=3)[CH:13]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].[K+].[C:27]([C:29]1[N:30]=[C:31]([C:42]([O-])=[O:43])[N:32]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH:33]=1)#[N:28].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>>[C:19]1([C:14]2[CH:13]=[C:12]([C:9]3[CH:8]=[CH:7][C:6]([S:3](=[O:4])(=[O:5])[N:2]([CH3:25])[CH3:1])=[CH:11][CH:10]=3)[CH:17]=[CH:16][C:15]=2[NH:18][C:42]([C:31]2[N:32]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH:33]=[C:29]([C:27]#[N:28])[N:30]=2)=[O:43])[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=1

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 2733179PyBroP

HCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

HCID 68505491HCID 68505491, compound

Product 1

HCID 86609179HCID 86609179, compound

Procedure

The title compound was prepared from 4′-amino-3′-cyclohex-1-enyl-biphenyl-4-sulfonic acid dimethylamide (as prepared in the previous step, 64 mg, 0.17 mmol), potassium 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate (as prepared in Example 11, step (d), 60 mg, 0.19 mmol), PyBroP (117 mg, 0.350 mmol) and DIEA (69 μL, 0.39 mmol) according to the procedure in Example 11, step (f) (84 mg, 70%). Mass spectrum (ESI, m/z): Calcd. for C31H39N5O4SSi, 606.2 (M+H), found 605.9.

Sources & evidence

ORD record: ord-33a2e1407ae548b9bd187f8ef8eb6118
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790724B2

Reaction notes

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