Methanol → HCID 69187894, compound

HRID 1020274Notes

Reaction equation

HRID 1020274 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:14][N:13]=[C:12]([CH2:15][NH:16][CH3:17])[N:11]=1)=[O:8].CO.[CH3:23][C:24]1[C:28]([CH:29]=O)=[C:27]([CH3:31])[O:26][N:25]=1.C([BH3-])#N.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:23][C:24]1[C:28]([CH2:29][N:16]([CH2:15][C:12]2[N:11]=[C:10]([NH:9][C:7]([NH:6][CH2:5][C:4]3[CH:18]=[CH:19][CH:20]=[C:2]([F:1])[CH:3]=3)=[O:8])[S:14][N:13]=2)[CH3:17])=[C:27]([CH3:31])[O:26][N:25]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 2895763,5-Dimethyl-4-Isoxazolecarbaldehyde2×HCID 5003444Sodium cyanoborohydride2×HCID 58055092HCID 58055092, compound2×

Product 1

HCID 69187894HCID 69187894, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(3-Fluoro-benzyl)-3-(3-methylaminomethyl-[1,2,4]thiadiazol-5-yl)-urea (Intermediate XXVII) was taken up in DCM and methanol with 3,5-Dimethyl-isoxazole-4-carbaldehyde (2 eq.) and acetic acid (several drops). Reaction was stirred for several hours at ambient temperature. Sodium cyanoborohydride (2 eq.) was added at once and the reaction was stirred overnight at ambient temperature. An additional equivalent of 3,5-Dimethyl-isoxazole-4-carbaldehyde and sodium cyanoborohydride (2 eq.) was added and stirred 4 more hours. Crude r×n mixture was loaded directly onto a silica plug and eluted with 10% saturated NH3/MeOH in DCM. Purified by column chromatography (silica, DCM, 0-10% MeOH saturated with NH3) to give the title compound. 1H NMR (400 MHz, DMSO): 11.45 (br s, 1H), 7.43-7.35 (m, 2H), 7.17-7.05 (m, 3H), 4.38 (d, 2H), 3.58 (s, 2H), 3.33 (s, 2H), 2.31 (s, 3H), 2.16 (s, 3H), 2.15 (s, 3H).

Workup

  1. customReaction
  2. stirringwas stirred overnight at ambient temperature
  3. stirringstirred 4 more hours
  4. washeluted with 10% saturated NH3/MeOH in DCM
  5. customPurified by column chromatography (silica, DCM, 0-10% MeOH saturated with NH3)

Sources & evidence

ORD record
ord-81710926290a45569c2e8327ca1ed29d
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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