2-Amino-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide → 5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(2-hydroxy-1-morpholin-4-ylpropyl)pyridin-2-yl]amino}thiophene-3-carboxamide

HRID 385792Notes

Reaction equation

HRID 385792 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:19])([CH3:18])[CH3:17])=[CH:12][C:11]=2[F:20])=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].Br[C:22]1[N:27]=[C:26]([CH:28]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:29]([OH:31])[CH3:30])[CH:25]=[CH:24][CH:23]=1>>[F:20][C:11]1[CH:12]=[C:13]([C:16]([OH:19])([CH3:17])[CH3:18])[CH:14]=[CH:15][C:10]=1[C:4]1[S:3][C:2]([NH:1][C:22]2[CH:23]=[CH:24][CH:25]=[C:26]([CH:28]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[CH:29]([OH:31])[CH3:30])[N:27]=2)=[C:6]([C:7]([NH2:9])=[O:8])[CH:5]=1

Participants

3

Reactant 2

HCID 582166382-Amino-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamideHCID 595262691-(6-Bromopyridin-2-yl)-1-morpholin-4-ylpropan-2-ol

Product 1

HCID 595255955-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(2-hydroxy-1-morpholin-4-ylpropyl)pyridin-2-yl]amino}thiophene-3-carboxamide

Procedure

The title compound was prepared as described in Example 1 using 2-amino-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide (150 mg, 0.510 mmol) and 1-(6-bromopyridin-2-yl)-1-morpholin-4-ylpropan-2-ol (168 mg, 0.510 mmol) as starting materials. 1H NMR (600 MHz, d6-DMSO): δ 11.96 (s, 1H), 7.84 (s, 1H), 7.81 (s, 1H), 7.66 (t, 1H), 7.54 (m, 1H), 7.36 (s, 1H), 7.32 (d, 1H), 7.31 (s, 1H), 7.95 (d, 1H), 6.78 (d, 1H), 5.13 (s, 1H), 4.55 (m, 1H), 4.18 (s, 1H), 3.54 (m, 4H), 3.31 (d, 1H), 2.61 (m, 2H), 2.33 (m, 2H), 1.40 (s, 6H), 0.89 (d, 3H). Calc'd for C26H32FN4O4S [M+H]+: 515. found 515.

Sources & evidence

ORD record
ord-05d03d2a7b5249c49c6efcac55542cba
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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