Sodium cyanoborohydride → HCID 15983550, compound

HRID 255204Notes

Reaction equation

HRID 255204 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:22]3[CH:23]=[C:24]([O:27][CH3:28])[CH:25]=[CH:26][C:21]=3[O:20][CH2:19][C:18]2=[O:29])[CH2:11][CH2:10]1.[O:30]=[C:31]1[CH2:36][O:35][C:34]2[CH:37]=[CH:38][C:39]([CH:41]=O)=[N:40][C:33]=2[NH:32]1.C([BH3-])#N.[Na+]>>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]2[O:20][CH2:19][C:18](=[O:29])[N:17]([CH2:16][CH2:15][N:12]3[CH2:11][CH2:10][CH:9]([NH:8][CH2:41][C:39]4[CH:38]=[CH:37][C:34]5[O:35][CH2:36][C:31](=[O:30])[NH:32][C:33]=5[N:40]=4)[CH2:14][CH2:13]3)[C:22]=2[CH:23]=1

Participants

4

Reactant 3

HCID 5003444Sodium cyanoborohydride2×HCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 667745864-[2-(4-aminopiperidin-1-yl)ethyl]-6-methoxy-2H-1,4-benzoxazin-3(4H)-one trifluoroacetate2×

Product 1

HCID 15983550HCID 15983550, compound

Procedure

4-[2-(4-aminopiperidin-1-yl)ethyl]-6-methoxy-2H-1,4-benzoxazin-3(4H)-one trifluoroacetate (Intermediate 46) (0.4 mmol), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (WO 2004/058144) (80 mg, 0.44 mmol) and sodium cyanoborohydride were reacted as described under Example 21, but, the reaction was stirred at room temperature overnight after sodium cyanoborohydride addition to give the title compound as a free base, 30 mg (17%).

Sources & evidence

ORD record
ord-d069599ae1c94d0489ef87475b843918
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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