HCID 53262182, compound → HCID 53262239, compound

HRID 1509188Notes

Reaction equation

HRID 1509188 reaction equation
NC1(C2C=CC(C3C(C4C=CC=CC=4)=CC4N(CCC#N)C(=O)COC=4N=3)=CC=2)CCC1.C(OC(=O)[NH:39][C:40]1([C:44]2[CH:49]=[CH:48][C:47]([C:50]3[C:51]([C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)=[CH:52][C:53]4[N:58]([CH2:59][CH2:60][CH2:61][CH2:62][C:63]#[N:64])[C:57](=[O:65])[CH2:56][O:55][C:54]=4[N:66]=3)=[CH:46][CH:45]=2)[CH2:43][CH2:42][CH2:41]1)(C)(C)C>>[NH2:39][C:40]1([C:44]2[CH:45]=[CH:46][C:47]([C:50]3[C:51]([C:67]4[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=4)=[CH:52][C:53]4[N:58]([CH2:59][CH2:60][CH2:61][CH2:62][C:63]#[N:64])[C:57](=[O:65])[CH2:56][O:55][C:54]=4[N:66]=3)=[CH:48][CH:49]=2)[CH2:43][CH2:42][CH2:41]1

Participants

3

Reactant 2

HCID 53262182HCID 53262182, compoundHCID 123705666HCID 123705666, compound

Product 1

HCID 53262239HCID 53262239, compoundYield 71.2%

Procedure

Following the procedure for 3-(6-(4-(1-aminocyclobutyl)phenyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)propanenitrile, tert-butyl(1-(4-(1-(4-cyanobutyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (25 mg, 0.045 mmol) was reacted to afford the title compound (14.5 mg). 1H NMR (500 MHz, CH3OD) 7.60 (1H, s), 7.42 (2H, d), 7.39 (2H, d), 7.31 (3H, m), 7.25 (2H, m), 4.97 (2H, s), 4.11 (2H, t), 2.73-2.79 (2H, m), 2.54-2.61 (4H, m), 2.22-2.25 (1H, m), 1.95-1.97 (1H, m), 1.84-1.89 (2H, m), 1.74-1.78 (2H, m). LCMS (Method A): RT=4.19 min, M+H+=453.5.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-54db84decc2d4847bf0a3a76bac6fddc
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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