Sodium cyanoborohydride → HCID 178487286, compound

HRID 255231Notes

Reaction equation

HRID 255231 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][CH2:9][N:10]2[C:15]3[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][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+]>>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]2[O:13][CH2:12][C:11](=[O:22])[N:10]([CH2:9][CH2:8][C@H:5]3[CH2:6][CH2:7][C@H: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)[CH2:3][CH2:4]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 178487285HCID 178487285, compound2×

Product 1

HCID 178487286HCID 178487286, compoundYield 24%

Procedure

4-[2-(Trans-4-aminocyclohexyl)ethyl]-6-methoxy-2H-1,4-benzoxazin-3(4H)-one (Intermediate 74) (310 mg, 1.73 mmol), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (WO 2004/058144) (1.73 mmol) and sodium cyanoborohydride were reacted as described under Example 21 to give 110 mg (24%) product.

Sources & evidence

ORD record
ord-ec80c55d016744e2b96e91402fcd9bfb
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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