Acetic Acid → N-(3-Fluoro-4-(2-(5-((2-methoxyethoxy)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-(4-fluorophenyl)acetamide

HRID 1401348Notes

Reaction equation

HRID 1401348 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:26][C:27]([NH:29][C:30](=[O:39])[CH2:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)=[S:28])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][N:19]=3)[S:17][C:10]=12.[CH3:40][O:41][CH2:42][CH2:43]N.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:26][C:27]([NH:29][C:30](=[O:39])[CH2:31][C:32]2[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=2)=[S:28])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][O:25][CH2:43][CH2:42][O:41][CH3:40])=[CH:20][N:19]=3)[S:17][C:10]=12

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 25212245N-(3-Fluoro-4-(2-(5-formylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-(4-fluorophenyl)acetamide

Product 1

HCID 25212242N-(3-Fluoro-4-(2-(5-((2-methoxyethoxy)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-(4-fluorophenyl)acetamideYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of aldehyde 33 (17.06 g, 30.04 mmol) and 2-methoxyethylamine (13.25 ml, 152 mmol) in THF (300 ml) in a 1 L round-bottom flask was added AcOH (8.71 ml, 152 mmol)). After 1 h, NaBH(OAc)3 (32.2 g, 152 mmol) was added and the reaction mixture was stirred for 20 h at r.t. and was then quenched with HCl 2M (300 mL) After 1 h, NaOH 2N (350 mL) was added until pH 11 and the mixture was concentrated. The solid was subjected to chromatographic purification through a pad of silica gel, eluent 2%-10% MeOH/DCM, to give 15 (8.59 g, 13.86 mmol, 81% yield) as a white solid. MS (m/z): 620.2 (M+1)

Workup

  1. customwas then quenched with HCl 2M (300 mL) After 1 h
  2. additionNaOH 2N (350 mL) was added until pH 11
  3. concentrationthe mixture was concentrated
  4. customThe solid was subjected to chromatographic purification through a pad of silica gel, eluent 2%-10% MeOH/DCM

Sources & evidence

ORD record
ord-ce2b944cc3444ce19c492c6943497248
Source dataset
uspto-grants-2014_12
Patent number
US08907091B2

Reaction notes

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