Methylamine → HCID 76281851, compound

HRID 2168290Notes

Reaction equation

HRID 2168290 reaction equation
CN.[C:3]([C:5]1[CH:6]=[CH:7][C:8]([F:36])=[C:9]([C@:11]23[CH2:20][O:19][C@@H:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[CH:22]=4)[CH2:17][C@H:16]2[CH2:15][S:14][C:13]([NH:27]C(=O)C2C=CC=CC=2)=[N:12]3)[CH:10]=1)#[N:4]>C(O)C>[NH2:27][C:13]1[S:14][CH2:15][C@@H:16]2[CH2:17][C@H:18]([C:21]3[O:25][N:24]=[C:23]([CH3:26])[CH:22]=3)[O:19][CH2:20][C@:11]2([C:9]2[CH:10]=[C:5]([CH:6]=[CH:7][C:8]=2[F:36])[C:3]#[N:4])[N:12]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86762656N-[(4aR,6R,8aS)-8a-(5-cyano-2-fluorophenyl)-6-(3-methyl-1,2-oxazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Product 1

HCID 76281851HCID 76281851, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methylamine (8 M in ethanol, 1.34 mmol) was added to a solution of N-[(4aR,6R,8aS)-8a-(5-cyano-2-fluorophenyl)-6-(3-methyl-1,2-oxazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (C37) (0.051 g, 0.11 mmol) in ethanol (4 mL). The resulting solution was allowed to stir at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure to give a yellow oily residue. Purification via silica gel chromatography (Gradient: 0% to 15% methanol in dichloromethane) afforded the product as an off-white solid. Yield: 25 mg, 63%. LCMS m/z 373.1 [M+H+]. 1H NMR (400 MHz, CD3OH) δ 7.78 (ddd, J=8.5, 4.5, 2.2 Hz, 1H), 7.69 (dd, J=7.2, 2.2 Hz, 1H), 7.35 (dd, J=8.6, 11.3 Hz, 1H), 6.26 (s, 1H), 4.89 (dd, J=11.9, 2.5 Hz, 1H), 4.25 (dd, J=11.2, 2.2 Hz, 1H), 3.80 (d, J=11.2 Hz, 1H), 3.08-3.14 (m, 1H), 2.89 (dd, J=12.7, 4.1 Hz, 1H), 2.78 (dd, J=12.7, 2.9 Hz, 1H), 2.28 (s, 3H), 2.10-2.22 (m, 1H), 1.91-1.96 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a yellow oily residue
  3. customPurification via silica gel chromatography (Gradient: 0% to 15% methanol in dichloromethane)

Sources & evidence

ORD record
ord-70f3c567d8d844aabe0910192f8775ec
Source dataset
uspto-grants-2015_06
Patent number
US09045498B2

Reaction notes

Loading…