Diisopropylethylamine → HCID 178424487, compound

HRID 1711309Notes

Reaction equation

[CH3:1][C:2]1([CH3:25])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([CH2:14][C:15]3[N:19]([Sn](C)(C)C)[N:18]=[N:17][N:16]=3)[CH:11]=[CH:10][C:9]=2[NH2:24])=[CH:4][CH2:3]1.[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>>[CH3:1][C:2]1([CH3:25])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([CH2:14][C:15]3[NH:19][N:18]=[N:17][N:16]=3)[CH:11]=[CH:10][C:9]=2[NH:24][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])=[CH:4][CH2:3]1

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 2733179PyBroP

HCID 587548812-(4,4-Dimethyl-cyclohex-1-enyl)-4-(1-trimethylstannanyl-1H-tetrazol-5-ylmethyl)-phenylamine

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

Product 1

HCID 178424487HCID 178424487, compound

Procedure

The title compound was prepared from 2-(4,4-dimethyl-cyclohex-1-enyl)-4-(1-trimethylstannanyl-1H-tetrazol-5-ylmethyl)-phenylamine (as prepared in the previous step, 280 mg, 0.626 mmol), potassium 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate (as prepared in Example 11, step (d), 267 mg, 1.56 mmol), PyBroP (466 mg, 1.00 mmol) and DIEA (273 μL, 1.56 mmol) according to the procedure in Example 11, step (f) (128 mg, 38%). 1H-NMR (CDCl3; 400 MHz): δ9.72 (s, 1H), 8.27 (d, 1H, J=8.3 Hz), 7.76 (s, 1H), 7.19 (m, 1H), 7.12 (s, 1H), 5.94 (s, 2H), 5.70 (s, 1H), 4.29 (s, 2H), 3.66-3.64 (m, 2H), 2.27-2.25 (m, 2H), 2.07-2.06 (m, 2H), 1.56-1.51 (m, 2H), 1.09 (s, 6H), 0.99-0.94 (m, 2H), 0.01 (s, 9H).

Sources & evidence

ORD record: ord-1a40ce9a961f47c5a19aa03a1971be4b
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790724B2

Reaction notes

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