Water → 5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(hydroxymethyl)pyrimidin-2-yl)thiophene-2-sulfonamide

HRID 1484944Notes

Reaction equation

HRID 1484944 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[C:24]([CH:26]4[CH2:28][CH2:27]4)[NH:23][N:22]=3)[C:17]([CH2:29][OH:30])=[CH:16][N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C.B(Cl)(Cl)Cl.O.CCOC(C)=O>C(Cl)Cl>[CH:26]1([C:24]2[NH:23][N:22]=[C:21]([NH:20][C:18]3[C:17]([CH2:29][OH:30])=[CH:16][N:15]=[C:14]([C:11]4[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=4)[N:19]=3)[CH:25]=2)[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25135Boron TrichlorideHCID 50943613N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(hydroxymethyl)pyrimidin-2-yl)thiophene-2-sulfonamide

Product 1

HCID 581695785-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(hydroxymethyl)pyrimidin-2-yl)thiophene-2-sulfonamideYield 74.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(hydroxymethyl) pyrimidin-2-yl) thiophene-2-sulfonamide (89 mg, 0.17 mmol, 1.0 eq) and BCl3 (1.0 ml, 1.0 mmol, 6.0 equiv.) in CH2Cl2 (5 mL) was stirred for 1 h at 0° C. After addition od water and extraction with EtOAc (3×50 ml), the combined organic phases were washed (brine), dried (Na2SO4), filtered and concentrated to produce 5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(hydroxymethyl)pyrimidin-2-yl)thiophene-2-sulfonamide (Compound 171) (50.0 mg, 74.8%) as white solid. LC-MS (m/z)=393.0 [M+H]+; 1H 1H NMR (400 MHz, DMSO-d6): δ 0.75-0.76 (m, 2H), 0.97-0.99 (m, 2H), 1.92-1.96 (m, 1H), 4.56 (d, J=5.2 Hz, 2H), 5.61 (t, J=5.2 Hz, 1H), 6.53 (d, J=10.4 Hz, 1H), 7.58 (d, J=3.6 Hz, 1H), 7.78 (s, 3H), 8.24 (s, 1H), 8.95 (s, 1H), 12.16 (s, 1H).

Workup

  1. washthe combined organic phases were washed (brine)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ab15a9ed87a746b1b8b30a9f25bccad2
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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