5-Bromopentanenitrile → HCID 123705666, compound

HRID 1509187Notes

Reaction equation

[C:1]([O:5][C:6](=[O:39])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:20][C:21]4[N:26]([CH2:27]CC#N)[C:25](=[O:31])[CH2:24][O:23][C:22]=4[N:32]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].O=C1COC2N=[C:48](C3C=CC(C4(NC(=O)OC(C)(C)C)CCC4)=CC=3)[C:49](C3C=CC=CC=3)=[CH:50][C:43]=2[NH:42]1.BrCCCCC#N>>[C:1]([O:5][C:6](=[O:39])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[CH:20][C:21]4[N:26]([CH2:27][CH2:48][CH2:49][CH2:50][C:43]#[N:42])[C:25](=[O:31])[CH2:24][O:23][C:22]=4[N:32]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 794355-Bromopentanenitrile

HCID 67256382HCID 67256382, compound

HCID 123769430HCID 123769430, compound

Product 1

HCID 123705666HCID 123705666, compound

Procedure

Following the procedure for tert-butyl(1-(4-(1-(2-cyanoethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate, tert-butyl 1-(4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutylcarbamate (100 mg, 0.212 mmol) was reacted with 5-bromopentanenitrile (103 mg, 0.636 mmol) to afford the title compound (82 mg. 1H NMR (500 MHz, CDCl3): 7.20-7.33 (10H, m), 5.03 (1H, br), 4.91 (2H, s), 4.05 (2H, t), 2.45-2.51 (6H, m), 2.05-2.10 (1H, m), 1.88-1.94 (2H, m), 1.67-1.85 (3H, m), 1.27-1.38 (9H, br).

Sources & evidence

ORD record: ord-7231b37df4b24c78b16c127f239679fe
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

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