Methylamine → HCID 58055082, compound

HRID 1685037Notes

Reaction equation

HRID 1685037 reaction equation
[BH4-].[Na+].[CH3:3][NH2:4].[F:5][C:6]1[CH:7]=[C:8]([CH:24]=[CH:25][CH:26]=1)[CH2:9][NH:10][C:11]([NH:13][C:14]1[S:15][C:16]([CH:21]([CH3:23])[CH3:22])=[C:17]([CH:19]=O)[N:18]=1)=[O:12]>>[F:5][C:6]1[CH:7]=[C:8]([CH:24]=[CH:25][CH:26]=1)[CH2:9][NH:10][C:11]([NH:13][C:14]1[S:15][C:16]([CH:21]([CH3:23])[CH3:22])=[C:17]([CH2:19][NH:4][CH3:3])[N:18]=1)=[O:12]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 86661300HCID 86661300, compound

Product 1

HCID 58055082HCID 58055082, compound

Procedure

NaBH4 (100 mg, 3 mmol) was added in portions to a mixture of MeNH2 (5 mL, 30% in EtOH) and 1-(3-fluorobenzyl)-3-(4-formyl-5-isopropylthiazol-2-yl)urea (322 mg, 1 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 1-(3-fluorobenzyl)-3-(5-isopropyl-4-((methylamino)methyl)thiazol-2-yl)urea. MS (ES+): M/Z 337 (M+H)+.

Workup

  1. customthen quenched with dilute HCl solution

Sources & evidence

ORD record
ord-a2c5213e82024284b46110260612c248
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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