5-(Tert-butoxycarbonylamino)-2-(3-fluoropyridin-2-yl)thiazole-4-carboxylic acid → N-[5-(4-acetamido-4-methyl-azepan-1-yl)-1-methyl-pyrazol-4-yl]-5-amino-2-(3-fluoro-2-pyridyl)thiazole-4-carboxamide

HRID 1915925Notes

Reaction equation

HRID 1915925 reaction equation
[CH3:1][C:2]1([NH:18][C:19](=[O:21])[CH3:20])[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][C:10]=2[N+:15]([O-])=O)[CH2:4][CH2:3]1.C(OC([NH:29][C:30]1[S:34][C:33]([C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][N:36]=2)=[N:32][C:31]=1[C:42](O)=[O:43])=O)(C)(C)C>>[C:19]([NH:18][C:2]1([CH3:1])[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][C:10]=2[NH:15][C:42]([C:31]2[N:32]=[C:33]([C:35]3[C:40]([F:41])=[CH:39][CH:38]=[CH:37][N:36]=3)[S:34][C:30]=2[NH2:29])=[O:43])[CH2:4][CH2:3]1)(=[O:21])[CH3:20]

Participants

3

Reactant 2

HCID 698113535-(Tert-butoxycarbonylamino)-2-(3-fluoropyridin-2-yl)thiazole-4-carboxylic acidHCID 86680019HCID 86680019, compound

Product 1

HCID 86680125N-[5-(4-acetamido-4-methyl-azepan-1-yl)-1-methyl-pyrazol-4-yl]-5-amino-2-(3-fluoro-2-pyridyl)thiazole-4-carboxamideYield 29%

Procedure

Following the procedures in Example 378, starting from N-(4-methyl-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)acetamide and 5-(tert-butoxycarbonylamino)-2-(3-fluoropyridin-2-yl)thiazole-4-carboxylic acid gave 384 as an off-white foam (80 mg, 29% over three steps). 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.41 (d, J=4.3 Hz, 1H), 7.90 (s, 1H), 7.52 (t, J=9.7 Hz, 1H), 7.31 (dt, J=8.4, 4.3 Hz, 1H), 6.32 (s, 2H), 5.75 (s, 1H), 3.74 (s, 3H), 3.33-3.15 (m, 4H), 2.38-2.21 (m, 2H), 2.02-1.84 (m, 4H), 1.82-1.74 (m, 3H), 1.51 (s, 3H). LCMS (ES+) m/z 487 (M+1)

Sources & evidence

ORD record
ord-9adff6d90fb84b77a281a8e8b944718a
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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