Diisopropylethylamine → 6-({4-[3-(7-Methoxy-2-oxo-2H-3,1-benzoxazin-1(4H)-yl)propyl]piperazin-1-yl}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 255281Notes

Reaction equation

HRID 255281 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:29]=[CH:28][C:13]2[CH2:14][O:15][C:16](=[O:27])[N:17]([CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:12]=2[CH:11]=1.C(N(CC)C(C)C)(C)C.[O:39]=[C:40]1[CH2:45][O:44][C:43]2[CH:46]=[CH:47][C:48]([CH:50]=O)=[N:49][C:42]=2[NH:41]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CO>[CH3:8][O:9][C:10]1[CH:29]=[CH:28][C:13]2[CH2:14][O:15][C:16](=[O:27])[N:17]([CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24]([CH2:50][C:48]4[CH:47]=[CH:46][C:43]5[O:44][CH2:45][C:40](=[O:39])[NH:41][C:42]=5[N:49]=4)[CH2:23][CH2:22]3)[C:12]=2[CH:11]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 667736227-Methoxy-1-(3-piperazin-1-ylpropyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one trifluoroacetate2×

Product 1

HCID 159822776-({4-[3-(7-Methoxy-2-oxo-2H-3,1-benzoxazin-1(4H)-yl)propyl]piperazin-1-yl}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

7-Methoxy-1-(3-piperazin-1-ylpropyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one trifluoroacetate (Intermediate 118, crude, 886 mg, 1.66 mmol) was converted to the free base with N,N-diisopropylethylamine and reacted with 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (WO 2004/058144) (220 mg, 1.23 mmol) and sodium triacetoxy borohydride (521 mg, 2.46 mmol) as described for Example 55 to give the free base of the product as a pink foam after chromatography on silica gel with dichloromethane/methanol (93:7), 86 mg (21%).

Sources & evidence

ORD record
ord-65c3750f167a4b119db25f0a0e096239
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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