Boron Trichloride → HCID 178436789, compound

HRID 1484958Notes

Reaction equation

HRID 1484958 reaction equation
B(Cl)(Cl)Cl.C([NH:9][S:10]([C:13]1[S:14][C:15]([C:18]2[N:23]=[C:22]([NH:24][C:25]3[CH:29]=[C:28]([CH:30]4[CH2:32][CH2:31]4)[NH:27][N:26]=3)[C:21]([C:33]#[CH:34])=[C:20]([CH3:35])[N:19]=2)=[CH:16][CH:17]=1)(=[O:12])=[O:11])(C)(C)C>C(Cl)Cl>[CH:30]1([C:28]2[CH:29]=[C:25]([NH:24][C:22]3[C:21]([C:33]#[CH:34])=[C:20]([CH3:35])[N:19]=[C:18]([C:15]4[S:14][C:13]([S:10]([NH2:9])(=[O:12])=[O:11])=[CH:17][CH:16]=4)[N:23]=3)[NH:26][N:27]=2)[CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 58169145HCID 58169145, compound

Product 1

HCID 178436789HCID 178436789, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BCl3 (1 M in CH2Cl2, 2.5 mL, 2.5 mmol, 5 eq) was added to a stirred solution of N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynyl-6-methyl pyrimidin-2-yl)thiophene-2-sulfonamide (230 mg, 0.50 mmol, 1.0 eq) in CH2Cl2 (10 mL) at rt under nitrogen. The reaction mixture was stirred for 30 min and then quenched with aq. NaHCO3 in ice bath. The reaction mixture was extracted with ethyl acetate and washed with water, brine, dried and evaporated. The crude product was crystallized with THF/isopropanol to afford the title compound 5-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-5-ethynyl-6-methylpyrimidin-2-yl)thiophene-2-sulfonamide (Compound 267) (175.0 mg, 87.5%). LC-MS (m/z)=401.1 [M+H]+. δ (400 MHz, DMSO-d6): 0.81-0.85 (m, 2H), 1.03-1.07 (m, 2H), 1.99-2.04 (m, 1H), 2.55 (s, 3H), 5.17 (s, 1H), 6.49 (s, 1H), 7.61 (d, J=3.6 Hz, 1H), 7.88 (s, 2H), 7.91 (d, J=3.6 Hz, 1H), 9.21 (s, 1H)

Workup

  1. customquenched with aq. NaHCO3 in ice bath
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washwashed with water, brine
  4. customdried
  5. customevaporated
  6. customThe crude product was crystallized with THF/isopropanol

Sources & evidence

ORD record
ord-e2ab9c45de4c48d49418d0e3d7075154
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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