Sodium cyanoborohydride → HCID 15983812, compound

HRID 255227Notes

Reaction equation

HRID 255227 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:15]3[CH:16]=[C:17]([F:21])[CH:18]=[C:19]([F:20])[C:14]=3[O:13][CH2:12][C:11]2=[O:22])[CH2:4][CH2:3]1.[O:23]=[C:24]1[CH2:29][O:28][C:27]2[CH:30]=[CH:31][C:32]([CH:34]=O)=[N:33][C:26]=2[NH:25]1.C([BH3-])#N.[Na+]>>[F:21][C:17]1[CH:18]=[C:19]([F:20])[C:14]2[O:13][CH2:12][C:11](=[O:22])[N:10]([CH2:9][CH2:8][N:5]3[CH2:4][CH2:3][CH:2]([NH:1][CH2:34][C:32]4[CH:31]=[CH:30][C:27]5[O:28][CH2:29][C:24](=[O:23])[NH:25][C:26]=5[N:33]=4)[CH2:7][CH2:6]3)[C:15]=2[CH:16]=1

Participants

4

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 66774613HCID 66774613, compound2×

Product 1

HCID 15983812HCID 15983812, compoundYield 8.7%

Procedure

4-[2-(4-Aminopiperidin-1-yl)ethyl]-6,8-difluoro-2H-1,4-benzoxazin-3(4H)-one (Intermediate 71) (1 mmol), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (WO 2004/058144) (220 mg, 1.24 mmol) and sodium cyanoborohydride (130 mg, 2.1 mmol) were reacted as described for Example 21 to give 41 mg (8%) product as a dry film.

Sources & evidence

ORD record
ord-d1966cca750b4c618014e6614c02f80b
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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