Methanol → 1-(4-((2,2-Difluoroethylamino)methyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea

HRID 1685038Notes

Reaction equation

HRID 1685038 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15]I)[N:14]=1)=[O:8].[F:20][CH:21]([F:24])[CH2:22][NH2:23].CO>C1COCC1>[F:20][CH:21]([F:24])[CH2:22][NH:23][CH2:15][C:13]1[N:14]=[C:10]([NH:9][C:7]([NH:6][CH2:5][C:4]2[CH:17]=[CH:18][CH:19]=[C:2]([F:1])[CH:3]=2)=[O:8])[S:11][CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1362742,2-Difluoroethanamine2×HCID 580550601-(3-Fluorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea3×

Product 1

HCID 866613011-(4-((2,2-Difluoroethylamino)methyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Iodomethyl-thiazol-2-yl)-3-(3-fluorobenzyl)-urea (Intermediate 7, 1 eq.) was taken up in THF (0.3 M) and 2,2-difluoroethanamine (20 eq.) was added. The reaction was stirred overnight at ambient temperature. Some of the starting material, Intermediate 7 remained. Added additional 2,2-difluoroethanamine (10 equivalents). The reaction was complete after 2-4 hours. Removed solvent; coevaporated twice with MeOH. Crude is a 1:1 mixture of title compound and bis addition impurity. (used as is in subsequent step).

Workup

  1. waitThe reaction was complete after 2-4 hours

Sources & evidence

ORD record
ord-23a8236c8abc42bfa8f3095b1966b861
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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