tert-butyl rel-{(3R,4R)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate → rel-5-{[(3R,4R)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt

HRID 1504899Notes

Reaction equation

HRID 1504899 reaction equation
BrC1C=C(N[C@@H]2[C@H](NC(=O)OC(C)(C)C)CCS(=O)(=O)C2)C=NC=1C#N.[OH:27][C:28]([C:30]([F:33])([F:32])[F:31])=[O:29].[NH2:34][C@H:35]1[CH2:40][CH2:39][S:38](=[O:42])(=[O:41])[CH2:37][C@H:36]1[NH:43][C:44]1[CH:45]=[C:46]([NH:53][C:54]2[CH:59]=[C:58]([O:60][CH3:61])[CH:57]=[C:56]([CH3:62])[N:55]=2)[C:47]([C:50]([NH2:52])=[O:51])=[N:48][CH:49]=1>>[OH:29][C:28]([C:30]([F:33])([F:32])[F:31])=[O:27].[NH2:34][C@@H:35]1[CH2:40][CH2:39][S:38](=[O:41])(=[O:42])[CH2:37][C@@H:36]1[NH:43][C:44]1[CH:45]=[C:46]([NH:53][C:54]2[CH:59]=[C:58]([O:60][CH3:61])[CH:57]=[C:56]([CH3:62])[N:55]=2)[C:47]([C:50]([NH2:52])=[O:51])=[N:48][CH:49]=1

Participants

3

Reactant 2

HCID 90354440tert-butyl rel-{(3R,4R)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamateHCID 131734339rel-5-{[(3S,4S)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-3-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt

Product 1

HCID 131734338rel-5-{[(3R,4R)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt

Procedure

rel-5-{[(3R,4R)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt (Enantiomer 2) was prepared from tert-butyl rel-{(3R,4R)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate (Enantiomer 2, from Step 2 of Example 20) using chemistry analogous to that described for the synthesis of rel-5-{[(3S,4S)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-3-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carboxamide (Example 20, Enantiomer 1). MS ESI calc'd. for C18H25N6O4S [M+H]+ 421. found 421. 1H NMR (500 MHz, DMSO-d6) δ 11.71 (s, 1H), 8.26-8.14 (m, 3H), 8.01 (s, 1H), 7.72 (s, 1H), 7.55-7.45 (br s, 1H), 6.74-6.20 (br s, 2H), 6.65 (s, 1H), 4.26 (s, 1H), 3.86-3.76 (m, 4H), 3.55-3.42 (m, 2H), 3.38-3.26 (m, 2H), 2.46-2.34 (m, 4), 2.30-2.21 (m, 1H).

Sources & evidence

ORD record
ord-7bd84e7694464a8da295c17c4218c952
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

Loading…