3,5-Dimethyl-4-Isoxazolecarbaldehyde → HCID 58055071, compound

HRID 1685080Notes

Reaction equation

HRID 1685080 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[C:8]([CH:9]=O)=[C:7]([CH3:11])[O:6][N:5]=1.Cl.[NH2:13][CH2:14][C:15]1[N:16]=[C:17]([NH:20][C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)=[O:22])[S:18][CH:19]=1>CO>[CH3:3][C:4]1[C:8]([CH2:9][NH:13][CH2:14][C:15]2[N:16]=[C:17]([NH:20][C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)=[O:22])[S:18][CH:19]=2)=[C:7]([CH3:11])[O:6][N:5]=1

Participants

5

Reactant 3

HCID 2895763,5-Dimethyl-4-IsoxazolecarbaldehydeHCID 4311764Sodium borohydrideHCID 86661313HCID 86661313, compound

Product 1

HCID 58055071HCID 58055071, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (35 mg, 1 mmol) was added in portions to a MeOH (5 mL) solution of 3,5-dimethylisoxazole-4-carbaldehyde (65 mg, 0.5 mmol) and 1-(4-(aminomethyl) thiazol-2-yl)-3-(3-fluorobenzyl)urea hydrochloride (157 mg, 0.5 mmol) at 0 C. The mixture was stirred for 6 hours then quenched with dilute HCl solution. Basic aqueous work-up with CH2Cl2 followed by flash chromatography afforded Intermediate 61: 1-(4-(((3,5-dimethylisoxazol-4-yl)methylamino)methyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea. 1H NMR (400 MHz, CDCl3): δ 8.2 (1H, br), 7.27 (m, 1H), 6.92 (m, 3H), 6.60 (s, 1H), 4.37 (d, 2H), 3.66 (s, 2H), 3.33 (s, 2H), 2.22 (s, 3H), 2.11 (s, 3H). MS (ES+): M/Z 390 (M+H)+.

Workup

  1. customthen quenched with dilute HCl solution

Sources & evidence

ORD record
ord-8e2bc4bdb53c41399610250f3cee2fa4
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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