Tetrahydro-4H-pyran-4-one → HCID 59750683, compound

HRID 422249Notes

Reaction equation

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

Participants

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-one

HCID 5003444Sodium cyanoborohydride

HCID 59750691HCID 59750691, compound2×

Product 1

HCID 59750683HCID 59750683, compoundYield 45.2%

Procedure

Using a method similar to Example 204, using 6-(5-aminomethyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy)nicotinamide (intermediate 20, 238 mg, 0.800 mmol), tetrahydro-4H-pyran-4-one (160 mg, 1.60 mmol), and NaBH3CN (100 mg, 1.60 mmol) gives the title compound (138 mg) as a white foam. Mass spectrum (ion spray): m/z=382 (M+1); 1HNMR (CDCl3): 8.57 (s, 1H), 8.16 (d, 1H), 7.23-7.16 (m, 2H), 6.94-6.90 (m, 2H), 5.86 (br. s, 2H), 4.00 (d, 2H), 3.40 (t, 2H), 3.15-2.78 (m, 3H), 2.65-2.41 (m, 2H), 1.97-1.46 (m, 9H).

Sources & evidence

ORD record: ord-69ac6a7e9ef04de0b5008eedb16931a2
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101638B2

Reaction notes

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