Methyl iodide → HCID 178424039, compound

HRID 2173999Notes

Reaction equation

[CH3:1][C:2]1[C:3]([CH:22]([OH:42])[C:23]2[N:27](COCC[Si](C)(C)C)[C:26]3[CH:36]=[CH:37][C:38]([C:40]#[N:41])=[CH:39][C:25]=3[N:24]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7](S(C1C=CC(C)=CC=1)(=O)=O)[CH:6]=[CH:5]2.CC1C(C(O)C2N(COCC[Si](C)(C)C)C3C=C(C#N)C=CC=3N=2)=C2C(=C(C)C=1)N(S(C1C=CC(C)=CC=1)(=O)=O)C=C2.Br[CH2:86][C:87]([O:89]C)=[O:88].CI>>[C:40]([C:38]1[CH:37]=[CH:36][C:26]2[NH:27][C:23]([CH:22]([C:3]3[C:2]([CH3:1])=[CH:10][C:9]([CH3:11])=[C:8]4[C:4]=3[CH:5]=[CH:6][NH:7]4)[O:42][CH2:86][C:87]([OH:89])=[O:88])=[N:24][C:25]=2[CH:39]=1)#[N:41]

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 60984Methyl bromoacetate

HCID 86701562HCID 86701562, compound

HCID 86701563HCID 86701563, compound

Product 1

HCID 178424039HCID 178424039, compound

Procedure

The title compound was synthesized from a mixture of (±)-2-((5,7-dimethyl-1-tosyl-1H-indol-4-yl)(hydroxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-((5,7-dimethyl-1-tosyl-1H-indol-4-yl)(hydroxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (Example 64-A) as described in Example 68 using methyl 2-bromoacetate as electrophile instead of methyl iodide. 1H NMR (TFA salt, 400 MHz, DMSO-d6) δ ppm 11.00 (br.s, 1H) 7.97 (s, 1H) 7.64 (d, J=8.33 Hz, 1H) 7.51-7.54 (m, 1H) 7.21 (t, J=2.78 Hz, 1H) 6.76 (s, 1H) 6.48-6.51 (m, 2H) 4.14 (A of AB, J=16.55 Hz, 1H) 3.99 (B of AB, J=16.55 Hz, 1H) 2.42 (s, 3H) 2.40 (s, 3H). HRMS calcd. for C21H18N4O3 (M+H)+ 375.1452. found 375.1465.

Sources & evidence

ORD record: ord-c3e029b7ce2448fcba5650338c344481
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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