Ammonia → (S)-3-chloro-1-fluoro-N7-(3-methylpyridin-2-yl)-5',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,4'-[1,3]oxazine]-2',7-diamine

HRID 931649Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([F:8])[C:5]2[O:9][C:10]3[C:15]([C@@:16]4([CH2:21][CH2:20][O:19]/[C:18](=[N:22]\C(=O)C5C=CC=CC=5)/[NH:17]4)[C:4]=2[CH:3]=1)=[CH:14][C:13]([NH:31][C:32]1[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][N:33]=1)=[CH:12][CH:11]=3.N.CO>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([F:8])[C:5]2[O:9][C:10]3[C:15]([C@@:16]4([CH2:21][CH2:20][O:19][C:18]([NH2:22])=[N:17]4)[C:4]=2[CH:3]=1)=[CH:14][C:13]([NH:31][C:32]1[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][N:33]=1)=[CH:12][CH:11]=3

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (S,Z)—N-(3-chloro-1-fluoro-7-((3-methylpyridin-2-yl)amino)spiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazinan]-2′-ylidene)benzamide (0.069 g, 0.130 mmol) in THF (2 mL) was added ammonia, 2.0M solution in methanol (10 ml, 20.00 mmol) and heated in a sealed tube at 50° C. for 15 h. The reaction was concentrated and purified by HPLC to afford (S)-3-chloro-1-fluoro-N7-(3-methylpyridin-2-yl)-5′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine as a white solid. MS m/z=426.1 [M+H]+.

Workup

concentrationThe reaction was concentrated
custompurified by HPLC

Sources & evidence

ORD record: ord-93efc3c1cf6e4482a34cd53db95f4b36
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296759B2

Reaction notes

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