N,N-Dimethylglycine → HCID 70657466, compound

HRID 872690Notes

Reaction equation

HRID 872690 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[Cl:8][C:9]1[CH:10]=[C:11]([C:17]2[CH:21]=[CH:20][N:19]([CH2:22][C@@H:23]([NH:25][C:26]([C:28]3[N:29]=[C:30]([CH2:33]O)[S:31][CH:32]=3)=[O:27])[CH3:24])[N:18]=2)[CH:12]=[CH:13][C:14]=1[C:15]#[N:16]>>[CH3:1][N:2]([CH3:7])[CH2:3][C:4]([O:6][CH2:33][C:30]1[S:31][CH:32]=[C:28]([C:26](=[O:27])[NH:25][C@@H:23]([CH3:24])[CH2:22][N:19]2[CH:20]=[CH:21][C:17]([C:11]3[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[C:9]([Cl:8])[CH:10]=3)=[N:18]2)[N:29]=1)=[O:5]

Participants

3

Reactant 2

HCID 673N,N-DimethylglycineHCID 67172696HCID 67172696, compound

Product 1

HCID 70657466HCID 70657466, compoundYield 39.5%

Procedure

(S)-(4-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl-carbamoyl)thiazol-2-yl)methyl 2-(dimethylamino)acetate was prepared using the method of Example 34(d) starting from N,N-dimethylglycine (0.062 g, 0.597 mmol) and (S)—N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-(hydroxymethyl)thiazole-4-carboxamide (0.2 g, 0.498 mmol). The product was triturated using diethyl ether and purified by Flash-chromatography, respectively. Yield 39.5%. 1H-NMR (400 MHz; CDCl3): δ 1.25 (d, 3H), 2.39 (s, 6H), 3.30 (s, 2H), 4.31 (dd, 1H), 4.43 (dd, 1H), 4.60 (m, 1H), 5.43 (d, 2H), 6.63 (d, 1H), 7.49 (d, 1H), 7.70 (d, 1H), 7.84 (dd, 1H), 7.95 (d, 1H), 7.97 (d, 1H), 8.12 (s, 1H).

Workup

  1. customThe product was triturated
  2. custompurified by Flash-chromatography

Sources & evidence

ORD record
ord-36b05bd0658d4fd5891e67291ab94102
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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