Bromoacetonitrile → HCID 90376271, compound

HRID 1507140Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]([CH2:18][C:19](=[O:23])[N:20]([CH3:22])[CH3:21])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:4]=1.[CH3:24][CH2:25][N:26](C(C)C)C(C)C.BrCC#N>>[C:25]([CH2:24][NH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]([CH2:18][C:19](=[O:23])[N:20]([CH3:22])[CH3:21])[C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:16])[CH3:14])[CH:4]=1)#[N:26]

Participants

Reactant 3

HCID 11534Bromoacetonitrile

HCID 81531Diisopropylethylamine

HCID 90375023HCID 90375023, compound

Product 1

HCID 90376271HCID 90376271, compound

Procedure

General Procedure T from tert-butyl N-{[4-(aminomethyl)pyridin-2-yl]methyl}-N-[(dimethylcarbamoyl)methyl]carbamate (1.0 equiv.), DIPEA (2.0 equiv.) and bromoacetonitrile (1.1 equiv.). Purification by preparative TLC (10% MeOH and 1% NH4OH in DCM) gave the title product as light yellow oil. 1H NMR (300 MHz, methanol-d4): δ ppm 8.42 (d, 1H), 7.46 (s, 1H), 7.33 (s, 1H), 4.58 (m, 2H), 4.19 (m, 2H), 3.93 (s, 2H), 3.65 (s, 2H), 2.98 (m, 6H), 1.42 (m, 9H).

Workup

customPurification by preparative TLC (10% MeOH and 1% NH4OH in DCM)

Sources & evidence

ORD record: ord-d0141e928a834960a5690aabbc1cd051
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221801B2

Reaction notes

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