Bromoacetonitrile → HCID 90375094, compound

HRID 1507150Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]2[CH2:25][CH2:24]2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:4]=1.Br[CH2:34][C:35]#[N:36].CCN(C(C)C)C(C)C>>[CH2:26]([N:22]([CH:23]1[CH2:25][CH2:24]1)[CH2:21][CH2:20][CH2:19][CH2:18][N:10]([CH2:9][C:5]1[CH:4]=[C:3]([CH2:2][NH:1][CH2:34][C:35]#[N:36])[CH:8]=[CH:7][N:6]=1)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Reactant 3

HCID 11534Bromoacetonitrile

HCID 81531Diisopropylethylamine

HCID 90375134HCID 90375134, compound

Product 1

HCID 90375094HCID 90375094, compound

Procedure

By General Procedure T from tert-butyl N-{[4-(aminomethyl)pyridin-2-yl]methyl}-N-{4-[benzyl(cyclopropyl)amino]butyl}carbamate (1 equiv.) and bromoacetonitrile (1.1 equiv.), using 2 equiv. DIPEA. Aqueous work up gave the title product, which was used without further purification.

Sources & evidence

ORD record: ord-c07c1059ad364468aa72a820725ea998
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221801B2

Reaction notes

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