Ammonia → (S)-3-chloro-1-fluoro-5',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,4'-[1,3]oxazine]-2',7-diamine

HRID 931641Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C@@:15]3([CH2:20][CH2:19][O:18]/[C:17](=[N:21]\C(=O)C4C=CC=CC=4)/[NH:16]3)[C:14]3[CH:13]=[C:12]([Cl:30])[N:11]=[C:10]([F:31])[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.N.CO>C1COCC1>[Cl:30][C:12]1[N:11]=[C:10]([F:31])[C:9]2[O:8][C:5]3[C:4]([C@@:15]4([CH2:20][CH2:19][O:18][C:17]([NH2:21])=[N:16]4)[C:14]=2[CH:13]=1)=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=3

Participants

Conditions

Temperature: 50 °C

Procedure

(S,Z)—N-(7-amino-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazinan]-2′-ylidene)benzamide was dissolved in THF (5 mL) followed by the addition of ammonia, 2.0 m solution in methanol (49.7 ml, 99 mmol) and heated in a sealed tube at 50° C. for 17 h. The mixture was concentrated and chromatographed on silica gel using 0-5% MeOH/DCM to afford a yellow oil as (S)-3-chloro-1-fluoro-5′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine (0.23 g, 0.687 mmol, 17% yield).

Workup

concentrationThe mixture was concentrated
customchromatographed on silica gel using 0-5% MeOH/DCM

Sources & evidence

ORD record: ord-8ca071ffc62144349678e394ce9a34ff
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296759B2

Reaction notes

Loading…