Boron Trichloride → 3-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)benzene sulfonamide

HRID 1484899Notes

Reaction equation

HRID 1484899 reaction equation
B(Cl)(Cl)Cl.C([NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[N:24]=[C:23]([NH:25][C:26]3[NH:30][N:29]=[C:28]([CH:31]4[CH2:33][CH2:32]4)[CH:27]=3)[C:22]([C:34]#[CH:35])=[CH:21][N:20]=2)[CH:14]=1)(=[O:12])=[O:11])(C)(C)C>C(Cl)Cl>[CH:31]1([C:28]2[NH:29][N:30]=[C:26]([NH:25][C:23]3[C:22]([C:34]#[CH:35])=[CH:21][N:20]=[C:19]([C:15]4[CH:14]=[C:13]([S:10]([NH2:9])(=[O:11])=[O:12])[CH:18]=[CH:17][CH:16]=4)[N:24]=3)[CH:27]=2)[CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 178437110HCID 178437110, compound

Product 1

HCID 581695383-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)benzene sulfonamideYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BCl3 (1 M in CH2Cl2, 0.92 mL, 0.92 mmol, 5 equiv.) was added to a stirred solution of N-tert-butyl-3-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-5-ethynylpyrimidin-2-yl)benzenesulfonamide (80 mg, 0.18 mmol, 1.0 equiv.) in CH2Cl2 (20 mL) at room temperature under nitrogen. The reaction mixture was stirred for 30 min and quenched with aq. NaHCO3 under an ice bath. The reaction mixture was extracted with ethylacetate and washed with water, brine, dried, filtered and evaporated. The crude product was crystallized with THF/isopropyl to afford the title compound 3-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)benzene sulfonamide (Compound 110) (40 mg, 57%). LC-MS (m/z)=380.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.82 (m, 2H), 0.96-0.98 (m, 2H), 1.94 (m, 1H), 4.90 (s, 1H), 6.47 (s, 1H), 7.45 (s, 2H), 7.74 (t, J=8.0 Hz, 1H), 7.97 (d, J=7.6 Hz, 1H), 8.49 (d, J=8.0 Hz, 1H), 8.62 (s, 1H), 8.70 (s, 1H), 8.82 (s, 1H), 12.31 (s, 1H).

Workup

  1. customquenched with aq. NaHCO3 under an ice bath
  2. extractionThe reaction mixture was extracted with ethylacetate
  3. washwashed with water, brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was crystallized with THF/isopropyl

Sources & evidence

ORD record
ord-ce59e6a878f04cf1946a40e6a5c24581
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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