2-Aminothiazole → N-Ethyl-1,3-thiazol-2-amine

HRID 419067Notes

Reaction equation

HRID 419067 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:16]=2)(=[O:14])=[O:13])[C:5]([C:8](O)=[O:9])=[N:6][CH:7]=1.[CH2:26]([NH:28][C:29]1[S:30][CH:31]=[CH:32][N:33]=1)[CH3:27].N[C:35]1[S:36][CH:37]=[CH:38][N:39]=1.[BH3-]C#N.[Na+].CN(C(O[N:52]1N=N[C:54]2C=CC=N[C:53]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH2:26]([NH:28][C:29]1[S:30][CH:31]=[CH:32][N:33]=1)[CH3:27].[Cl:1][C:2]1[C:3]([C:35]2[S:36][CH:37]=[CH:38][N:39]=2)=[C:4]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]([F:23])([F:25])[F:24])[CH:16]=2)(=[O:13])=[O:14])[C:5]([C:8]([NH:52][CH2:53][CH3:54])=[O:9])=[N:6][CH:7]=1

Participants

8

Reactant 6

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 13699275N-Ethyl-1,3-thiazol-2-amineHCID 579420775-Chloro-3-(4-chloro-3-trifluoromethyl benzenesulfonylamino)-pyridine-2-carboxylic acid

Product 2

HCID 13699275N-Ethyl-1,3-thiazol-2-amineHCID 666489565-Chloro-3(4-chloro-3-(trifluoromethyl)phenysulfonamido)-N-ethyl-(thiazol-2-yl)picolinamide

Procedure

5-Chloro-3-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)picolinic acid (120 mg, 0.3 mmol), 2-ethylaminothiazole [(50 mg, 0.4 mmol) 2-Ethylaminothiazole was prepared freshly from 2-aminothiazole and acetylaldehyde via standard reductive amination condition using NaCNBH3 as the reducing agent], HATU (190 mg, 0.5 mmol), DIEA (130 mg, 1 mmol) were reacted according to the procedure D to provide the title compound. HPLC purification (20→90% gradient of MeCN-water) provided 5-Chloro-3(4-chloro-3-(trifluoromethyl)phenysulfonamido)-N-ethyl-(thiazol-2-yl)picolinamide: 1H NMR (400 MHz, CDCl3) δ 9.20 (s, 1H), 8.23 (s, 1H), 8.07 (s, 1H), 7.82 (d, 1H), 7.61 (s, 1H), 7.46 (d, 1H), 7.20 (s, 1H), 6.0 (s, 2H), 4.02 (q, 2H), 1.25 (t, 3H); MS m/z 525.0 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9119ceadf41c4b4e8e6cb8f633e793cb
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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