Sodium cyanoborohydride → HCID 15983680, compound

HRID 1644338Notes

Reaction equation

HRID 1644338 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]([O:20][C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:19][C:14]=3[O:13][CH2:12][C:11]2=[O:25])[CH2:4][CH2:3]1.[O:26]=[C:27]1[CH2:32][O:31][C:30]2[CH:33]=[CH:34][C:35]([CH:37]=O)=[N:36][C:29]=2[NH:28]1.C([BH3-])#N.[Na+]>>[O:25]=[C:11]1[N:10]([CH2:9][CH2:8][N:5]2[CH2:4][CH2:3][CH:2]([NH:1][CH2:37][C:35]3[CH:34]=[CH:33][C:30]4[O:31][CH2:32][C:27](=[O:26])[NH:28][C:29]=4[N:36]=3)[CH2:7][CH2:6]2)[C:15]2[CH:16]=[C:17]([O:20][C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:19][C:14]=2[O:13][CH2:12]1

Participants

4

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 66775194HCID 66775194, compound2×

Product 1

HCID 15983680HCID 15983680, compoundYield 15.3%

Procedure

4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-(trifluoromethoxy)-2H-1,4-benzoxazin-3(4H)-one (Intermediate 61) (0.55 mmol), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (WO 2004/058144) (120 mg, 0.66 mmol) and sodium cyanoborohydride (69 mg, 1.1 mmol) were reacted as described under Example 21 to give 44 mg (15%) product as a solid.

Sources & evidence

ORD record
ord-69c6d35ff9024107a0d16a8be3d2ef93
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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