3-amino-5-hydroxyquinoxalin-2(1H)-one → (S)-3-amino-5-(6-chloro-2-(1-methoxypropan-2-ylamino)pyrimidin-4-yloxy)quinoxalin-2(1H)-one

HRID 2056708Notes

Reaction equation

HRID 2056708 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C@@H:10]([CH3:14])[CH2:11][O:12][CH3:13])[N:3]=1.[NH2:15][C:16]1[C:17](=[O:27])[NH:18][C:19]2[C:24]([N:25]=1)=[C:23]([OH:26])[CH:22]=[CH:21][CH:20]=2>>[NH2:15][C:16]1[C:17](=[O:27])[NH:18][C:19]2[C:24]([N:25]=1)=[C:23]([O:26][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C@@H:10]([CH3:14])[CH2:11][O:12][CH3:13])[N:3]=1)[CH:22]=[CH:21][CH:20]=2

Participants

3

Reactant 2

HCID 167483403-amino-5-hydroxyquinoxalin-2(1H)-oneHCID 58612018(s)-4,6-Dichloro-n-(1-methoxypropan-2-yl)pyrimidin-2-amine

Product 1

HCID 58612053(S)-3-amino-5-(6-chloro-2-(1-methoxypropan-2-ylamino)pyrimidin-4-yloxy)quinoxalin-2(1H)-one

Procedure

The reaction of (S)-4,6-dichloro-N-(1-methoxypropan-2-yl)pyrimidin-2-amine from step (a) above (0.62 g, 2.63 mmol) with 3-amino-5-hydroxyquinoxalin-2(1H)-one (0.47 g, 3 mmol, prepared as described in WO 2004/014871) under the conditions of Example 105(a) provided the title compound as an off-white solid. MS (ESI, pos. ion.) m/z: 377 (M+1).

Sources & evidence

ORD record
ord-9bcbbfd85efa488bb305e782563c80dd
Source dataset
uspto-grants-2008_02
Patent number
US07335672B2

Reaction notes

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