Methylamine → HCID 59272447, compound

HRID 558156Notes

Reaction equation

[F:1][C:2]1[C:3]([C:16]2[S:20][C:19]3[C:21]([C:25]4[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=4[CH:27]=O)=[CH:22][CH:23]=[CH:24][C:18]=3[CH:17]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[N:12]2)=[N:6][CH:7]=1.[C:33]([BH3-])#[N:34].CC(C)(C)C(O)=O.CN>O1CCOCC1.C(Cl)(Cl)Cl.CC(O)C>[N:11]1([CH2:10][CH2:9][NH:8][C:5]2[N:4]=[C:3]([C:16]3[S:20][C:19]4[C:21]([C:25]5[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=5[CH2:27][NH:34][CH3:33])=[CH:22][CH:23]=[CH:24][C:18]=4[CH:17]=3)[C:2]([F:1])=[CH:7][N:6]=2)[CH:15]=[CH:14][N:13]=[N:12]1

Participants

Conditions

Temperature: 100 °C

Procedure

Combine 2-{2-[5-fluoro-2-(2-[1,2,3]triazol-1-yl-ethylamino)-pyrimidin-4-yl]-benzo[b]thiophen-7-yl}-benzaldehyde (800 mg, 1.8 mmol), cyanoborohydride (silica supported, 1 mmol/g, 2.7 g, 2.7 mmol), trimethylacetic acid (0.55 g, 4.7 mmol), and mono-methylamine (0.42 g, 5.4 mmol) in 12 mL of dioxane. Heat the reaction mixture at 100° C. for 20 min in microwave reactor. Cool it to RT. Dilute with chloroform/IPA (3:1, v/v), 50 mL. Wash with water, aqueous saturated sodium chloride, and dry over magnesium sulfate. Remove the organic solvent. Purify the residue by column chromatography [chloroform/methanol/ammonium hydroxide (35% in water), 7/3/0.05] to give the title compound (425 mg, 38%). MS (ES) m/z 460 [M+1]+.

Workup

temperatureCool it to RT
washWash with water, aqueous saturated sodium chloride
dry with materialdry over magnesium sulfate
customRemove the organic solvent
customPurify the residue by column chromatography [chloroform/methanol/ammonium hydroxide (35% in water), 7/3/0.05]

Sources & evidence

ORD record: ord-e9dddd12263e4b169c94bcd4ab744f9a
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063035B2

Reaction notes

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