HCID 58169313, compound → HCID 50943863, compound

HRID 1484952Notes

Reaction equation

HRID 1484952 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:8]([NH:26][C:27]2[CH:31]=[C:30]([CH:32]3[CH2:34][CH2:33]3)[NH:29][N:28]=2)=[N:9][C:10]([C:13]2[S:14][C:15]([S:18](=[O:25])(=[O:24])[NH:19]C(C)(C)C)=[CH:16][CH:17]=2)=[N:11][CH:12]=1)(=[O:3])[CH3:2]>C(O)(C(F)(F)F)=O>[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:8]([NH:26][C:27]2[CH:31]=[C:30]([CH:32]3[CH2:34][CH2:33]3)[NH:29][N:28]=2)=[N:9][C:10]([C:13]2[S:14][C:15]([S:18](=[O:24])(=[O:25])[NH2:19])=[CH:16][CH:17]=2)=[N:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 58169313HCID 58169313, compound

Product 1

HCID 50943863HCID 50943863, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The solution of 2-(2-(5-(N-tert-butylsulfamoyl)thiophen-2-yl)-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-5-yl)ethyl acetate (300 mg, 0.6 mmol) in CF3COOH (5 mL) was stirred at 60° C. After 1 h, the solution was evaporated to afford 2-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-(5-sulfamoylthiophen-2-yl)pyrimidin-5-yl)ethyl acetate (Compound 313) (250 mg, 93%). LC-MS (m/z)=449 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.76 (m, 2H), 0.98-0.99 (m, 2H), 1.94 (m, 1H), 1.99 (s, 3H), 2.98 (s, 2H), 4.20 (s, 2H), 6.47 (s, 1H), 7.59 (s, 1H), 7.76 (d, J=2.8 Hz, 1H), 7.81 (s, 2H), 8.16 (s, 1H), 9.44 (s, 1H).

Workup

  1. customthe solution was evaporated

Sources & evidence

ORD record
ord-06d44dd040ed43e49ffac0e49bc509d0
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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