Methanol → HCID 59291672, compound

HRID 1809613Notes

Reaction equation

HRID 1809613 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[N:14]=[C:13]([NH:15][C:16]3[N:21]=[CH:20][C:19]([O:22][C:23]4[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=4)=[CH:18][C:17]=3[S:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:38])[S:12][N:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CO.[BH4-].[Na+].[NH4+].[Cl-]>CCOC(C)=O>[Cl:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[S:31][C:17]1[C:16]([NH:15][C:13]2[S:12][N:11]=[C:10]([CH:7]3[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]3)[N:14]=2)=[N:21][CH:20]=[C:19]([O:22][C:23]2[CH:24]=[CH:25][C:26]([CH2:27][OH:28])=[CH:29][CH:30]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86641106HCID 86641106, compound

Product 1

HCID 59291672HCID 59291672, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(6-(3-(1-Acetylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-chlorophenylthio)pyridin-3-yloxy)benzaldehyde (30 mg, 0.0530 mmol) was dissolved in 1:1 EtOAc:methanol (2 mL) and NaBH4 (10.0 mg, 0.265 mmol) was added. After stirring 30 minutes the reaction was poured into aqueous NH4Cl, extracted with EtOAc and purified on silica gel (0 to 10% methanol in EtOAc) to afford 1-(4-(5-(3-(2-chlorophenylthio)-5-(4-(hydroxymethyl)phenoxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone (19.9 mg, 0.0350 mmol, 66.1% yield) as a white solid. 1H NMR (CDCl3) δ 9.23 (s, 1H), 8.30 (d, 1H), 7.64 (d, 1H), 7.43 (m, 1H), 7.38 (d, 2H), 7.16 (m, 2H), 7.01 (d, 2H), 6.76 (dd, 1H), 4.69 (d, 2H), 4.57 (d, 1H), 3.88 (d, 1H), 3.20 (t, 1H), 3.03 (m, 1H), 2.80 (t, 1H), 2.11 (s, 3H), 2.07 (m, 2H), 1.92-1.71 (m, 3H).

Workup

  1. extractionextracted with EtOAc
  2. custompurified on silica gel (0 to 10% methanol in EtOAc)

Sources & evidence

ORD record
ord-2bae18335744473b96b232210f3bc328
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

Loading…